Download PDF
Christmann, M. et al.: 2020 Science of Synthesis, 2020/1: Knowledge Updates 2020/1 DOI: 10.1055/sos-SD-104-00551
Knowledge Updates 2020/1

4.4.40.72 Allylsilanes (Update 2020)

More Information

Book

Editors: Christmann, M.; Huang, Z.; Jiang, X.; Li, J.-J.; Oestreich, M.; Petersson, E. J.; Schaumann, E.; Wang, M.

Authors: Bode, J. W.; Cabrera, M.; Howlader, A. H.; Huang, Z.; Liang, Y.; Liu, G.; Maison, W.; Ohe, K.; Okamoto, K.; Osuna Gálvez, A.; Wen, Z.; Wnuk, S. F.; Wu, F.; Zhu, S.

Title: Knowledge Updates 2020/1

Print ISBN: 9783132435582; Online ISBN: 9783132435605; Book DOI: 10.1055/b000000102

1st edition © 2020 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

This chapter is an update to the earlier Science of Synthesis contribution (Section 4.4.40), which describes methods for the synthesis of allylsilanes as well as their applications in organic synthesis. This update summarizes the recently reported (from 2001 to 2018) efficient synthetic methods and synthetic applications of allylsilanes involving transition-metal-catalyzed reactions.

Key words

allylsilanes - vinylsilanes - alkenes - allenes - dienes - silanes - carbonyl compounds - cycloaddition reactions - organosilicon chemistry - transition-metal catalysis
 
  • 1 Hosomi A, Miura K. Bull. Chem. Soc. Jpn. 2004; 77: 835
  • 2 Chabaud L, James P, Landais Y. Eur. J. Org. Chem. 2004; 3173
  • 3 Barbero A, Pulido FJ. Acc. Chem. Res. 2004; 37: 817
    PubMed
  • 4 Barbero A, Pulido FJ, Sañudo MC. Beilstein J. Org. Chem. 2007; 3: 16
    PubMed
  • 5 Terao J, Kambe N. Chem. Rec. 2007; 7: 57
    PubMed
  • 6 Schmidt AW, Knölker H.-J. Synlett 2010; 2207
  • 7 Leighton JL. Aldrichimica Acta 2010; 43: 3
  • 8 Brook MA, Mohamed M. Helv. Chim. Acta 2012; 95: 2660
  • 9 Ramachandran PV, Nicponski DR, Gagare PD, In: Comprehensive Organic Synthesis Knochel P, Molander GA. Elsevier Oxford 2014; 2. 72
  • 10 Motokura K, Baba T. Green Chem. 2012; 14: 565
  • 11 Han JW, Hayashi T. Tetrahedron: Asymmetry 2010; 21: 2193
  • 12 Taguchi T, Saito A, Yanai H. Chem. Rec. 2007; 7: 167
    PubMed
  • 13 Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2011; 111: 7774
    PubMed
  • 14 Archibald SC, Barden DJ, Bazin JFY, Fleming I, Foster CF, Mandal AK, Mandal AK, Parker D, Takaki K, Ware AC, Williams ARB, Zwicky AB. Org. Biomol. Chem. 2004; 2: 1051
    PubMed
  • 15 Suginome M, Ito Y. J. Organomet. Chem. 2003; 680: 43
  • 16 Díez-Poza C, Barbero A. Eur. J. Org. Chem. 2017; 4651
  • 17 Majo VJ, Suzuki S, Toyota M, Ihara M. J. Chem. Soc., Perkin Trans. 1 2000; 3375
  • 18 Furman B, Dziedzic M. Tetrahedron Lett. 2003; 44: 8249
  • 19 Purser S, Odell B, Claridge TDW, Moore PR, Gouverneur V. Chem.–Eur. J. 2006; 12: 9176
    PubMed
  • 20 Terao J, Watabe H, Watanabe H, Kambe N. Adv. Synth. Catal. 2004; 346: 1674
  • 21 Naitoh Y, Bando F, Terao J, Otsuki K, Kuniyasu H, Kambe N. Chem. Lett. 2007; 36: 236
  • 22 Kabalka GW, Venkataiah B, Dong G. Organometallics 2005; 24: 762
  • 23 Moser R, Nishikata T, Lipshutz BH. Org. Lett. 2010; 12: 28
    PubMed
  • 24 Selander N, Paasch JR, Szabó KJ. J. Am. Chem. Soc. 2011; 133: 409
    PubMed
  • 25 Larsson JM, Szabó KJ. J. Am. Chem. Soc. 2013; 135: 443
    PubMed
  • 26 Oestreich M, Auer G. Adv. Synth. Catal. 2005; 347: 637
  • 27 Magnus P, Rainey T, Lynch V. Tetrahedron Lett. 2003; 44: 2459
  • 28 O’Brien M, Taylor NH, Thomas EJ. Tetrahedron Lett. 2002; 43: 5491
  • 29 Vyas DJ, Oestreich M. Chem. Commun. (Cambridge) 2010; 46: 568
    PubMed
  • 30 Hensel A, Oestreich M. Chem.–Eur. J. 2015; 21: 9062
    PubMed
  • 31 Vyas DJ, Oestreich M. Angew. Chem. Int. Ed. 2010; 49: 8513
    PubMed
  • 32 Delvos LB, Vyas DJ, Oestreich M. Angew. Chem. Int. Ed. 2013; 52: 4650
    PubMed
  • 33 Takeda M, Shintani R, Hayashi T. J. Org. Chem. 2013; 78: 5007
    PubMed
  • 34 Xuan Q.-Q, Zhong N.-J, Ren C.-L, Liu L, Wang D, Chen Y.-J, Li C.-J. J. Org. Chem. 2013; 78: 11 076
  • 35 Ito H, Horita Y, Sawamura M. Adv. Synth. Catal. 2012; 354: 813
  • 36 Bourque LE, Cleary PA, Woerpel KA. J. Am. Chem. Soc. 2007; 129: 12 602
  • 37 Streiff S, Ribeiro N, Désaubry L. J. Org. Chem. 2004; 69: 7592
    PubMed
  • 38 Streiff S, Ribeiro N, Désaubry L. Chem. Commun. (Cambridge) 2004; 346
    PubMed
  • 39 Liepins V, Bäckvall J.-E. Org. Lett. 2001; 3: 1861
    PubMed
  • 40 Han JW, Hayashi T. Chem. Lett. 2001; 976
  • 41 Han JW, Hayashi T. Tetrahedron: Asymmetry 2002; 13: 325
  • 42 Terao J, Oda A, Ikumi A, Nakamura A, Kuniyasu H, Kambe N. Angew. Chem. Int. Ed. 2003; 42: 3412
    PubMed
  • 43 Gerdin M, Moberg C. Org. Lett. 2006; 8: 2929
    PubMed
  • 44 Kimura M, Tamaru Y, In: Modern Organonickel Chemistry Tamaru Y. Wiley-VCH Weinheim, Germany 2005; 137-170
  • 45 Fukushima M, Takushima D, Kimura M. J. Am. Chem. Soc. 2010; 132: 16 346 ; and references therein
  • 46 Saito N, Kobayashi A, Sato Y. Angew. Chem. Int. Ed. 2012; 51: 1228
    PubMed
  • 47 Lee K.-s, Wu H, Haeffner F, Hoveyda AH. Organometallics 2012; 31: 7823
    PubMed
  • 48 Hande SM, Nakajima M, Kamisaki H, Tsukano C, Takemoto Y. Org. Lett. 2011; 13: 1828
    PubMed
  • 49 Liepins V, Karlström ASE, Bäckvall J.-E. Org. Lett. 2000; 2: 1237
    PubMed
  • 50 Liepins V, Karlström ASE, Bäckvall J.-E. J. Org. Chem. 2002; 67: 2136
    PubMed
  • 51 Pulido FJ, Barbero A, García C. Tetrahedron 2009; 65: 5535
  • 52 Barbero A, García C, Pulido FJ. Tetrahedron 2000; 56: 2739
  • 53 Barbero A, Blanco Y, Pulido FJ. Chem. Commun. (Cambridge) 2001; 1606
    PubMed
  • 54 Barbero A, García C, Pulido FJ. Synlett 2001; 824
  • 55 Barbero A, Castreño P, García C, Pulido FJ. J. Org. Chem. 2001; 66: 7723
    PubMed
  • 56 Barbero A, Blanco Y, Pulido FJ. J. Org. Chem. 2005; 70: 6876
    PubMed
  • 57 Barbero A, Castreño P, Fernández G, Pulido FJ. J. Org. Chem. 2005; 70: 10 747
  • 58 Pulido FJ, Barbero A, Blanco Y. Org. Biomol. Chem. 2011; 9: 1454
    PubMed
  • 59 Yang F.-Y, Shanmugasundaram M, Chuang S.-Y, Ku P.-J, Wu M.-Y, Cheng C.-H. J. Am. Chem. Soc. 2003; 125: 12 576
  • 60 Suginome M, Ohmura T, Miyake Y, Mitani S, Ito Y, Murakami M. J. Am. Chem. Soc. 2003; 125: 11 174
  • 61 Ohmura T, Taniguchi H, Suginome M. J. Am. Chem. Soc. 2006; 128: 13 682
    PubMed
  • 62 Tani Y, Fujihara T, Terao J, Tsuji Y. J. Am. Chem. Soc. 2014; 136: 17 706
  • 63 Miller ZD, Li W, Belderrain TR, Montgomery J. J. Am. Chem. Soc. 2013; 135: 15 282
  • 64 Wang C, Teo WJ, Ge S. Nat. Commun. 2017; 8: 2258
    PubMed
  • 65 Asako S, Ishikawa S, Takai K. ACS Catal. 2016; 6: 3387
  • 66 Nakamura S, Uchiyama M, Ohwada T. J. Am. Chem. Soc. 2005; 127: 13 116
  • 67 Tamao K, Akita M, Kanatani R, Ishida N, Kumada M. J. Organomet. Chem. 1982; 226: C9
  • 68 Larsson JM, Zhao TSN, Szabó KJ. Org. Lett. 2011; 13: 1888
    PubMed
  • 69 Atienza CCH, Diao T, Weller KJ, Nye SA, Lewis KM, Delis JGP, Boyer JL, Roy AK, Chirik PJ. J. Am. Chem. Soc. 2014; 136: 12 108
    PubMed
  • 70 McAtee JR, Yap GPA, Watson DA. J. Am. Chem. Soc. 2014; 136: 10 166
  • 71 Mata S, López LA, Vicente R. Angew. Chem. Int. Ed. 2017; 56: 7930
    PubMed
  • 72 Da B.-C, Liang Q.-J, Luo Y.-C, Ahmad T, Xu Y.-H, Loh T.-P. ACS Catal. 2018; 8: 6239
  • 73 Suzuki H, Kuroda C. Tetrahedron 2003; 59: 3157
  • 74 Kamachi T, Kuno A, Matsuno C, Okamoto S. Tetrahedron Lett. 2004; 45: 4677
  • 75 Dunn J, Dobbs AP. Tetrahedron 2015; 71: 7386
  • 76 Dota K, Shimizu T, Hasegawa S, Miyashita M, Tanino K. Tetrahedron Lett. 2011; 52: 910
  • 77 Takahashi K, Takeda K, Honda T. Tetrahedron Lett. 2010; 51: 3542
  • 78 Uenishi J, Iwamoto T, Ohmi M. Tetrahedron Lett. 2007; 48: 1237
  • 79 Guo L, Leiendecker M, Hsiao C.-C, Baumann C, Rueping M. Chem. Commun. (Cambridge) 2015; 51: 1937
    PubMed
  • 80 Beszant S, Giannini E, Zanoni G, Vidari G. Eur. J. Org. Chem. 2003; 3958
  • 81 Hofstra JL, Cherney AH, Ordner CM, Reisman SE. J. Am. Chem. Soc. 2018; 140: 139
    PubMed
  • 82 Bhat NG, Lai WC, Carroll MB. Tetrahedron Lett. 2007; 48: 4267
  • 83 Zweifel G, Arzoumanian H, Whitney CC. J. Am. Chem. Soc. 1967; 89: 3652
  • 84 Matteson DS. Chem. Rev. 1989; 89: 1535
  • 85 Aggarwal VK, Binanzer M, Carolina de Cegile M, Gallanti M, Glasspoole BW, Kendrick SJF, Sonawane RP, Vázquez-Romero A, Webster MP. Org. Lett. 2011; 13: 1490
    PubMed
  • 86 Hodgeson DM, Fleming MJ, Stanway SJ. J. Org. Chem. 2007; 72: 4763
    PubMed
  • 87 Li W.-DZ, Yang J.-H. Org. Lett. 2004; 6: 1849
    PubMed
  • 88 Shen S.-J, Li W.-DZ. J. Org. Chem. 2013; 78: 7112
    PubMed
  • 89 Dowling MS, Vanderwal CD. J. Am. Chem. Soc. 2009; 131: 15 090
  • 90 Kumagai T, Itsuno S. Macromolecules 2000; 33: 4995
  • 91 Kumagai T, Itsuno S. Tetrahedron: Asymmetry 2001; 12: 2509
  • 92 Kumagai T, Itsuno S. Macromolecules 2001; 34: 7624
  • 93 Endo K, Sakamoto A, Ohkubo T, Shibata T. Chem. Lett. 2011; 40: 1440
  • 94 Peroche S, Remuson R, Gelas-Mialhe Y, Gramain J.-C. Tetrahedron Lett. 2001; 42: 4617
  • 95 Li D, Tanaka T, Ohmiya H, Sawamura M. Org. Lett. 2010; 12: 3344
    PubMed
  • 96 Kacprzynski MA, May TL, Kazane SA, Hoveyda AH. Angew. Chem. Int. Ed. 2007; 46: 4554
    PubMed
  • 97 Yasuda Y, Nagao K, Shido Y, Mori S, Ohmiya H, Sawamura M. Chem.–Eur. J. 2015; 21: 9666
    PubMed
  • 98 Shintani R, Ichikawa Y, Hayashi T, Chen J, Nakao Y, Hiyama T. Org. Lett. 2007; 9: 4643
    PubMed
  • 99 Shintani R, Okamoto K, Hayashi T. Org. Lett. 2005; 7: 4757
    PubMed
  • 100 Simon M.-O, Martinez R, Genêt J.-P, Darses S. Adv. Synth. Catal. 2009; 351: 153
  • 101 Binanzer M, Fang GY, Aggarwal VK. Angew. Chem. Int. Ed. 2010; 49: 4264
    PubMed
  • 102 Huh CW, Roush WR. Org. Lett. 2008; 10: 3371
    PubMed
  • 103 Shotwell JB, Roush WR. Org. Lett. 2004; 6: 3865
    PubMed
  • 104 Tinsley JM, Roush WR. J. Am. Chem. Soc. 2005; 127: 10 818
    PubMed
  • 105 Va P, Roush WR. J. Am. Chem. Soc. 2006; 128: 15 960
  • 106 Ohmura T, Ohshima K, Suginome M. Angew. Chem. Int. Ed. 2011; 50: 12 501
  • 107 Sawaki R, Sato Y, Mori M. Org. Lett. 2004; 6: 1131
    PubMed
  • 108 Li D, Liu G, Hu Q, Wang C, Xi Z. Org. Lett. 2007; 9: 5433
    PubMed
  • 109 Chen M, Roush WR. Org. Lett. 2011; 13: 1992
    PubMed
  • 110 Chai G, Zeng R, Fu C, Ma S. Eur. J. Org. Chem. 2013; 148
  • 111 Hazra CK, Oestreich M. Org. Lett. 2012; 14: 4010
    PubMed
  • 112 Johnson DA, Hendrix AJM, Jennings MP. J. Org. Chem. 2018; 83: 9914
    PubMed
  • 113 Rabten W, Margarita C, Eriksson L, Andersson PG. Chem.–Eur. J. 2018; 24: 1681
    PubMed
  • 114 Hirano K, Yorimitsu H, Oshima K. Org. Lett. 2006; 8: 483
    PubMed
  • 115 Yan D, Thomson MD, Backer M, Bolte M, Hahn R, Berger R, Fann W, Roskos HG, Auner N. Chem.–Eur. J. 2009; 15: 8625
    PubMed
  • 116 Kawachi A, Maeda H, Nakamura H, Doi N, Tamao K. J. Am. Chem. Soc. 2001; 123: 3143
  • 117 Suginome M, Iwanami T, Ito Y. J. Am. Chem. Soc. 2001; 123: 4356
    PubMed
  • 118 Judd WR, Ban S, Aubé J. J. Am. Chem. Soc. 2006; 128: 13 736
    PubMed
  • 119 Suginome M, Iwanami T, Ohmori Y, Matsumoto A, Ito Y. Chem.–Eur. J. 2005; 11: 2954
    PubMed
  • 120 Sieburth SMcN, O’Hare HK, Xu J, Chen Y, Liu G. Org. Lett. 2003; 5: 1859
    PubMed
  • 121 Liu G, Sieburth SMcN. Org. Lett. 2003; 5: 4677
    PubMed
  • 122 Nakazaki A, Nakai T, Tomooka K. Angew. Chem. Int. Ed. 2006; 45: 2235
    PubMed
  • 123 Mohamed M, Brook MA. Tetrahedron Lett. 2001; 42: 191
  • 124 Mohamed M, Brook MA. Helv. Chim. Acta 2002; 85: 4165
  • 125 McLaughlin MG, Cook MJ. J. Org. Chem. 2012; 77: 2058
    PubMed
  • 126 Henrion S, Carboni B, Cossío FP, Roisnel T, Villalgordo JM, Carreaux F. J. Org. Chem. 2016; 81: 4633
    PubMed
  • 127 Xie J, Horne DA. Tetrahedron Lett. 2009; 50: 4485
  • 128 Xie J, Ma Y, Horne DA. Tetrahedron 2011; 67: 7485
  • 129 Kolodziej I, Green JR. Org. Biomol. Chem. 2015; 13: 10 852
  • 130 Enomoto M, Kuwahara S. J. Org. Chem. 2006; 71: 6287
    PubMed
  • 131 Olsson VJ, Szabó KJ. Org. Lett. 2008; 10: 3129
    PubMed
  • 132 Arndt M, Reinhold A, Hilt G. J. Org. Chem. 2010; 75: 5203
    PubMed
  • 133 Fernández-Galán R, Hitchcock PB, Lappert MF, Antiñolo A, Rodríguez AM. J. Chem. Soc., Dalton Trans. 2000; 1743
  • 134 Leroy B, Dumeunier R, Markó IE. Tetrahedron Lett. 2000; 41: 10 215
  • 135 Dumeunier R, Leclercq C, Markó IE. Tetrahedron Lett. 2002; 43: 2307
  • 136 Markó IE, Dumeunier R, Leclercq C, Leroy B, Plancher J.-M, Mekhalfia A, Bayston DJ. Synthesis 2002; 958
  • 137 Kim M.-Y, Kim H, Tae J. Synlett 2009; 1303
  • 138 Cossy J, BouzBouz S, Hoveyda AH. J. Organomet. Chem. 2001; 634: 216
  • 139 Cossy J, BouzBouz S, Hoveyda AH. J. Organomet. Chem. 2001; 624: 327
  • 140 Rikimaru K, Mori K, Kan T, Fukuyama T. Chem. Commun. (Cambridge) 2005; 394
    PubMed
  • 141 Cassidy JH, Farthing CN, Marsden SP, Pederson A, Slater M, Stemp G. Org. Biomol. Chem. 2006; 4: 4118
    PubMed
  • 142 Guptill DM, Cohen CM, Davies HML. Org. Lett. 2013; 15: 6120
    PubMed
  • 143 Tietze LF, Thede K, Schimpf R, Sannicolò F. Chem. Commun. (Cambridge) 2000; 583
  • 144 Tietze LF, Völkel L, Wulff C, Weigand B, Bittner C, McGrath P, Johnson K, Schäfer M. Chem.–Eur. J. 2001; 7: 1304
    PubMed
  • 145 Tietze LF, Kahle K, Raschke T. Chem.–Eur. J. 2002; 8: 401
    PubMed
  • 146 Mohr P, Imhoff M.-P, Reggiani F. Tetrahedron Lett. 2015; 56: 2262
  • 147 Miyawaki A, Kikuchi D, Niki M, Manabe Y, Kanematsu M, Yokoe H, Yoshida M, Shishido K. J. Org. Chem. 2012; 77: 8231
    PubMed
  • 148 Organ MG, Dragan V, Miller M, Froese RDJ, Goddard JD. J. Org. Chem. 2000; 65: 3666
    PubMed
  • 149 Tori M, Makino C, Hisazumi K, Sono M, Nakashima K. Tetrahedron: Asymmetry 2001; 12: 301
  • 150 Toshima H, Oikawa H, Toyomasu T, Sassa T. Tetrahedron 2000; 56: 8443
  • 151 Huh CW, Somal GK, Katz CE, Pei H, Zeng Y, Douglas JT, Aubé J. J. Org. Chem. 2009; 74: 7618
    PubMed
  • 152 Kim MJ, Chun MW. Aust. J. Chem. 2007; 60: 291
  • 153 Chen C, Mariano PS. J. Org. Chem. 2000; 65: 3252
    PubMed
  • 154 Durand A.-C, Brahmi L, Lahrech M, Hacini S, Santelli M. Synth. Commun. 2005; 35: 1825
  • 155 Chung WJ, Welch JT. J. Fluorine Chem. 2004; 125: 543
  • 156 Monfray J, Gelas-Mialhe Y, Gramain J.-C, Remuson R. Tetrahedron: Asymmetry 2005; 16: 1025
  • 157 Keck GE, Welch DS, Poudel YB. Tetrahedron Lett. 2006; 47: 8267
  • 158 Reddy UC, Raju BR, Kumar EKP, Saikia AK. J. Org. Chem. 2008; 73: 1628
    PubMed
  • 159 Bandi CKR, Belostoskii A, Hassner A. Adv. Synth. Catal. 2014; 356: 2661
  • 160 Niimi L, Serita K.-i, Hiraoka S, Yokozawa T. Tetrahedron Lett. 2000; 41: 7075
  • 161 Yamasaki S, Fujii K, Wada R, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2002; 124: 6536
    PubMed
  • 162 Wang H, Zhao W. J. Chem. Res. 2011; 35: 310
  • 163 Nishimoto Y, Yasuda M, Baba A. Org. Lett. 2007; 9: 4931
    PubMed
  • 164 Fallan C, Quigley PF, Lam HW. J. Org. Chem. 2011; 76: 4112
    PubMed
  • 165 Wang MW, Chen YJ, Wang D. Heteroat. Chem. 2001; 12: 534
  • 166 Wadamoto M, Yamamoto H. J. Am. Chem. Soc. 2005; 127: 14 556
  • 167 Malkov AV, Bell M, Castelluzzo F, Kočovský P. Org. Lett. 2005; 7: 3219
    PubMed
  • 168 Malkov AV, Ramírez-López P, Biedermannová L, Rulíšek L, Dufková L, Kotora M, Zhu F, Kočovský P. J. Am. Chem. Soc. 2008; 130: 5341
    PubMed
  • 169 Hrdina R, Opekar F, Roithová J, Kotora M. Chem. Commun. (Cambridge) 2009; 2314
    PubMed
  • 170 Limnios D, Kokotos CG. Chem.–Eur. J. 2014; 20: 559
    PubMed
  • 171 Takeuchi K, Takeda T, Fujimoto T, Yamamoto I. Tetrahedron 2007; 63: 5319
  • 172 Kumagai T, Itsuno S. Macromol. Rapid Commun. 2001; 22: 741
  • 173 Itsuno T SKumagai. Synthesis 2002; 941
  • 174 Friestad GK, Ding H. Angew. Chem. Int. Ed. 2001; 40: 4491
    PubMed
  • 175 Dias LC, Meira PRR. Synlett 2000; 37
  • 176 Ghosh AK, Kulkarni SS, Xu C.-X, Shurrush K. Tetrahedron: Asymmetry 2008; 19: 1020
    PubMed
  • 177 Michellys P.-Y, Maurin P, Pellissier H, Santelli M. Tetrahedron Lett. 2002; 43: 4339
  • 178 Jagtap SB, Tsogoeva SB. Chem. Commun. (Cambridge) 2006; 4747
    PubMed
  • 179 Huber JD, Perl NR, Leighton JL. Angew. Chem. Int. Ed. 2008; 47: 3037
    PubMed
  • 180 Yamaguchi R, Nakayasu T, Hatano B, Nagura T, Kozima S, Fujita K.-i. Tetrahedron 2001; 57: 109
  • 181 Yamaguchi R, Tanaka M, Matsuda T, Okano T, Nagura T, Fujita K.-i. Tetrahedron Lett. 2002; 43: 8871
  • 182 Taketoshi A, Hosoda N, Yamaguchi Y, Asami M. Bull. Chem. Soc. Jpn. 2007; 80: 2418
  • 183 Friestad GK, Korapala CS, Ding H. J. Org. Chem. 2006; 71: 281
    PubMed
  • 184 Furman B, Dziedzic M. Tetrahedron Lett. 2003; 44: 6629
  • 185 Lee PH, Lee K, Sung S.-y, Chang S. J. Org. Chem. 2001; 66: 8646
    PubMed
  • 186 Shizuka M, Snapper ML. Angew. Chem. Int. Ed. 2008; 47: 5049
    PubMed
  • 187 Kataki D, Phukan P. Tetrahedron Lett. 2009; 50: 1958
  • 188 Yadav JS, Reddy BVS, Reddy GM, Narender R. Synlett 2009; 963
  • 189 Yasuda M, Onishi Y, Ito T, Baba A. Tetrahedron Lett. 2000; 41: 2425
  • 190 Tietze LF, Weigand B, Völkel L, Wulff C, Bittner C. Chem.–Eur. J. 2001; 7: 161
    PubMed
  • 191 Tietze LF, Hölsken S, Adrio J, Kinzel T, Wegner C. Synthesis 2004; 2236
  • 192 Pospíšil J, Kumamoto T, Markó IE. Angew. Chem. Int. Ed. 2006; 45: 3357
    PubMed
  • 193 Kang K.-T, Sung TM, Jung HC, Lee JG. Bull. Korean Chem. Soc. 2008; 29: 1669
  • 194 Hotoda K, Ohnuma A, Kusakabe K, Tanaka A, Sasaki I, Sugimura H. Tetrahedron Lett. 2016; 57: 5359
  • 195 Peng F, Grote RE, Wilson RM, Danishefsky SJ. Proc. Natl. Acad. Sci. U. S. A. 2013; 110: 10 904
    PubMed
  • 196 Yadav VK, Naganaboina VK, Hulikal V. Tetrahedron Lett. 2014; 55: 2015
  • 197 Giese S, Kastrup L, Stiens D, West FG. Angew. Chem. Int. Ed. 2000; 39: 1970
    PubMed
  • 198 Shenje R, Williams CW, Francois KM, France S. Org. Lett. 2014; 16: 6468
    PubMed
  • 199 Hossain MA, Jin M.-J, Donaldson WA. J. Organomet. Chem. 2001; 630: 5
  • 200 Jeon SL, Kim JK, Son JB, Kim BT, Jeong IH. Tetrahedron Lett. 2006; 47: 9107
  • 201 Laub HA, Yamamoto H, Mayr H. Org. Lett. 2010; 12: 5206
    PubMed
  • 202 O’Neill PM, Rawe SL, Storr RC, Ward SA, Posner GH. Tetrahedron Lett. 2005; 46: 3029
  • 203 Lu Y, Green JR. Synlett 2001; 243
  • 204 Köhler A, Raabe G, Runsink J, Köhler F, Gais H.-J. Eur. J. Org. Chem. 2014; 3355
  • 205 Schwier T, Rubin M, Gevorgyan V. Org. Lett. 2004; 6: 1999
    PubMed
  • 206 Fan X, Cui X.-M, Guan Y.-H, Fu L.-A, Lv H, Guo K, Zhu H.-B. Eur. J. Org. Chem. 2014; 498
  • 207 Porcel S, Loëpez-Carrillo V, Garciëa-Yebra C, Echavarren AM. Angew. Chem. Int. Ed. 2008; 47: 1883
    PubMed
  • 208 Hirano K, Fujita K, Yorimitsu H, Shinokubo H, Oshima K. Tetrahedron Lett. 2004; 45: 2555
  • 209 Luzung MR, Toste FD. J. Am. Chem. Soc. 2003; 125: 15 760
  • 210 Georgy M, Boucard V, Debleds O, Dal Zotto C, Campagne J.-M. Tetrahedron 2009; 65: 1758
  • 211 Yang C.-Y, Wang C.-D, Tian S.-F, Liu R.-S. Adv. Synth. Catal. 2010; 352: 1605
  • 212 Motokura K, Nakagiri N, Mizugaki T, Ebitani K, Kaneda K. J. Org. Chem. 2007; 72: 6006
    PubMed
  • 213 Yadav JS, Reddy BVS, Reddy AS, Eeshwaraiah B. Chem. Lett. 2007; 36: 1500
  • 214 Yadav JS, Reddy BVS, Rao TS, Rao KVR. Tetrahedron Lett. 2008; 49: 614
  • 215 Kumar GGKSN, Laali KK. Org. Biomol. Chem. 2012; 10: 7347
    PubMed
  • 216 Vicennati P, Cozzi PG. Eur. J. Org. Chem. 2007; 2248
  • 217 Peh GR, Floreancig PE. Org. Lett. 2015; 17: 3750
    PubMed
  • 218 Reddel JCT, Wang W, Koukounas K, Thomson RJ. Chem. Sci. 2017; 8: 2156
    PubMed
  • 219 Yamanoi T, Nara Y, Matsuda S, Oda Y, Yoshida A, Katsuraya K, Watanabe M. Synlett 2007; 785
  • 220 Hamilton JY, Hauser N, Sarlah D, Carreira EM. Angew. Chem. Int. Ed. 2014; 53: 10 759
  • 221 Jeker OF, Kravina AG, Carreira EM. Angew. Chem. Int. Ed. 2013; 52: 12 166
  • 222 Mariet N, Ibrahim-Ouali M, Santelli M. Tetrahedron Lett. 2003; 44: 5315
  • 223 Mariet N, Pellissier H, Ibrahim-Ouali M, Santelli M. Eur. J. Org. Chem. 2004; 2679
  • 224 Galy N, Moraleda D, Santelli M. Tetrahedron Lett. 2009; 50: 5238
  • 225 Galy N, Moraleda D, Santelli M. Tetrahedron 2011; 67: 1448
  • 226 Schmitt A, Reißig H.-U. Eur. J. Org. Chem. 2000; 3893
  • 227 Bear TJ, Shaw JT, Woerpel KA. J. Org. Chem. 2002; 67: 2056
    PubMed
  • 228 Nishikawa T, Mishima Y, Ohyabu N, Isobe M. Tetrahedron Lett. 2004; 45: 175
  • 229 Pansare SV, Adsool VA. Org. Lett. 2006; 8: 5897
    PubMed
  • 230 Cellier M, Gelas-Mialhe Y, Husson H.-P, Perrin B, Remuson R. Tetrahedron: Asymmetry 2000; 11: 3913
  • 231 Shirakawa S, Lombardi PJ, Leighton JL. J. Am. Chem. Soc. 2005; 127: 9974
    PubMed
  • 232 Allin SM, Northfield CJ, Page MI, Slawin AMZ. J. Chem. Soc., Perkin Trans. 1 2000; 1715
  • 233 Sarkar TK, Hazra A, Gangopadhyay P, Panda N, Slanina Z, Lin C.-C, Chen H.-T. Tetrahedron 2005; 61: 1155
  • 234 Pilli RA, Robello LG. Synlett 2005; 2297
  • 235 Leverett CA, Cassidy MP, Padwa A. J. Org. Chem. 2006; 71: 8591
    PubMed
  • 236 Conchon E, Gelas-Mialhe Y, Remuson R. Tetrahedron: Asymmetry 2006; 17: 1253
  • 237 Remuson R. Beilstein J. Org. Chem. 2007; 3: 32
    PubMed
  • 238 Epstein OL, Rovis T. J. Am. Chem. Soc. 2006; 128: 16 480
  • 239 Denmark SE, Werner NS. J. Am. Chem. Soc. 2008; 130: 16 382
  • 240 Amemiya R, Suwa K, Toriyama J, Nishimura Y, Yamaguchi M. J. Am. Chem. Soc. 2005; 127: 8252
    PubMed
  • 241 Shimizu R, Egami H, Hamashima Y, Sodeoka M. Angew. Chem. Int. Ed. 2012; 51: 4577
    PubMed
  • 242 Mizuta S, Galicia-López O, Engle KM, Verhoog S, Wheelhouse K, Rassias G, Gouverneur V. Chem.–Eur. J. 2012; 18: 8583
    PubMed
  • 243 Tinsley JM, Mertz E, Chong PY, Rarig R.-AF, Roush WR. Org. Lett. 2005; 7: 4245
    PubMed
  • 244 Peng Z.-H, Woerpel KA. Org. Lett. 2002; 4: 2945
    PubMed
  • 245 Saito A, Sakamoto W, Yanai H, Taguchi T. Tetrahedron Lett. 2006; 47: 4181
  • 246 Dey RT, Haque SA, Hazra A, Basak S, Sarkar TK. Tetrahedron Lett. 2007; 48: 6671
  • 247 Dey RT, Sarkar TK. J. Org. Chem. 2010; 75: 4521
    PubMed
  • 248 Schmidt AW, Olpp T, Schmid S, Goutal S, Jäger A, Knölker H.-J. Synlett 2007; 1549
  • 249 Schmidt AW, Olpp T, Schmid S, Jäger A, Knölker H.-J. Tetrahedron 2009; 65: 5484
  • 250 Okamoto K, Tamura E, Ohe K. Angew. Chem. Int. Ed. 2014; 53: 10 195
  • 251 Hanhan NV, Ball-Jones NR, Tran NT, Franz AK. Angew. Chem. Int. Ed. 2012; 51: 989
    PubMed
  • 252 Ball-Jones NR, Badillo JJ, Tran NT, Franz AK. Angew. Chem. Int. Ed. 2014; 53: 9462
    PubMed
  • 253 Shindoh N, Tokuyama H, Takasu K. Tetrahedron Lett. 2007; 48: 4749
  • 254 Nair V, Dhanya R, Vidya N, Devipriya S. Synthesis 2006; 107
  • 255 Matsumura Y, Suzuki T, Sakakura A, Ishihara K. Angew. Chem. Int. Ed. 2014; 53: 6131
    PubMed
  • 256 Lv J, Zhang L, Luo S, Cheng J.-P. Angew. Chem. Int. Ed. 2013; 52: 9786
    PubMed
  • 257 Angle SR, Belanger DS, El-Said NA. J. Org. Chem. 2002; 67: 7699
    PubMed
  • 258 Matsuo J.-i, Sasaki S, Hoshikawa T, Ishibashi H. Org. Lett. 2009; 11: 3822
    PubMed
  • 259 Shupe BH, Allen EE, MacDonald JP, Wilson SO, Franz AK. Org. Lett. 2013; 15: 3218
    PubMed
  • 260 MacDonald JP, Shupe BH, Schreiber JD, Franz AK. Chem. Commun. (Cambridge) 2014; 50: 5242
    PubMed
  • 261 Horino Y, Kimura M, Naito M, Tanaka S, Tamaru Y. Tetrahedron Lett. 2000; 41: 3427
  • 262 Kimura M, Horino Y, Mori M, Tamaru Y. Chem.–Eur. J. 2007; 13: 9686
    PubMed
  • 263 Takasu K, Hosokawa N, Inanaga K, Ihara M. Tetrahedron Lett. 2006; 47: 6053
  • 264 Inanaga K, Takasu K, Ihara M. J. Am. Chem. Soc. 2005; 127: 3668
    PubMed
  • 265 Okamoto K, Shimbayashi T, Tamura E, Ohe K. Org. Lett. 2015; 17: 5843
    PubMed
  • 266 Trost BM. Pure Appl. Chem. 1988; 60: 1615
  • 267 Trost BM, Cramer N, Silverman SM. J. Am. Chem. Soc. 2007; 129: 12 396
  • 268 Shintani R, Hayashi T. J. Am. Chem. Soc. 2006; 128: 6330
    PubMed
  • 269 Shintani R, Park S, Duan W.-L, Hayashi T. Angew. Chem. Int. Ed. 2007; 46: 5901
    PubMed
  • 270 Trost BM, Stambuli JP, Silverman SM, Schwörer U. J. Am. Chem. Soc. 2006; 128: 13 328
  • 271 Fernández-Rivas C, Méndez M, Nieto-Oberhuber C, Echavarren AM. J. Org. Chem. 2002; 67: 5197
    PubMed
  • 272 Horino Y, Luzung MR, Toste FD. J. Am. Chem. Soc. 2006; 128: 11 364
  • 273 Tokimizu Y, Oishi S, Fujii N, Ohno H. Org. Lett. 2014; 16: 3138
    PubMed
  • 274 Matsuda T, Kadowaki S, Yamaguchi Y, Murakami M. Chem. Commun. (Cambridge) 2008; 2744
    PubMed
  • 275 Yoshioka S, Fujii Y, Tsujino H, Uno T, Fujioka H, Arisawa M. Chem. Commun. (Cambridge) 2017; 53: 5970
    PubMed
  • 276 Kozuka M, Tsuchida T, Mitani M. Tetrahedron Lett. 2005; 46: 4527
  • 277 Tredwell M, Tenza K, Pacheco MC, Gouverneur V. Org. Lett. 2005; 7: 4495
    PubMed
  • 278 Stikute A, Peipiņš V, Turks M. Tetrahedron Lett. 2015; 56: 4578
  • 279 Beërard D, Racicot L, Sabot C, Canesi S. Synlett 2008; 1076
  • 280 Pulido FJ, Barbero A, Abad R. Eur. J. Org. Chem. 2011; 6974
  • 281 James P, Schenk K, Landais Y. J. Org. Chem. 2006; 71: 3630
    PubMed
  • 282 Macsári I, Szabó KJ. Tetrahedron Lett. 2000; 41: 1119
  • 283 Wilkinson SC, Lozano O, Schuler M, Pacheco MC, Salmon R, Gouverneur V. Angew. Chem. Int. Ed. 2009; 48: 7083
    PubMed
  • 284 Moore DL, Taylor MP, Timms PL. J. Chem. Soc., Dalton Trans. 2000; 2673
  • 285 Ferrini S, Cini E, Taddei M. Synlett 2013; 24: 491
  • 286 Yoshimura Y, Kan-no H, Kiran YB, Natori Y, Saito Y, Takahata H. Synthesis 2012; 44: 1163
  • 287 Allatabakhsh A, Pham M, Minehan T. Heterocycles 2007; 72: 115
  • 288 Imazeki S, Kinoshita R, Akiyama T. Bull. Chem. Soc. Jpn. 2007; 80: 972
  • 289 Yoshida J.-i, Watanabe M, Toshioka H, Imagawa M, Suga S. J. Electroanal. Chem. 2001; 507: 55
  • 290 Huang Y.-t, Moeller KD. Tetrahedron 2006; 62: 6536
  • 291 Kuroda C, Koshio H. Chem. Lett. 2000; 962
  • 292 Campbell JM, Smith JA, Gonzalez L, Moeller KD. Tetrahedron Lett. 2015; 56: 3595
  • 293 Strohmann C, Lehmen K, Dilsky S. J. Am. Chem. Soc. 2006; 128: 8102
    PubMed
  • 294 Oba M, Iida M, Nishiyama K. Organometallics 2001; 20: 4287
  • 295 Bouchez LC, Dubbaka SR, Turks M, Vogel P. J. Org. Chem. 2004; 69: 6413
    PubMed
  • 296 James P, Felpin F.-X, Landais Y, Schenk K. J. Org. Chem. 2005; 70: 7985
    PubMed
  • 297 Asao N, Chan CS, Takahashi K, Yamamoto Y. Tetrahedron 2005; 61: 11 322
  • 298 Agami C, Comesse S, Kadouri-Puchot C. J. Org. Chem. 2002; 67: 2424
    PubMed
  • 299 Jung ME, Piizzi G. J. Org. Chem. 2002; 67: 3911
    PubMed
  • 300 Lauchli R, Whitney JM, Zhu L, Shea KJ. Org. Lett. 2005; 7: 3913
    PubMed
  • 301 Huang Y.-t, Moeller KD. Org. Lett. 2004; 6: 4199
    PubMed
  • 302 Méndez M, Cuerva JM, Gómez-Bengoa E, Cárdenas DJ, Echavarren AM. Chem.–Eur. J. 2002; 8: 3620
    PubMed
  • 303 Suga S, Nishida T, Yamada D, Nagaki A, Yoshida J.-i. J. Am. Chem. Soc. 2004; 126: 14 338
  • 304 Iwasawa N, Otsuka M, Yamashita S, Aoki M, Takaya J. J. Am. Chem. Soc. 2008; 130: 6328
    PubMed
  • 305 Hughes NJ, Pullin RDC, Sanganee MJ, Sellars JD, Steel PG, Turner MJ. Org. Biomol. Chem. 2007; 5: 2841
    PubMed
  • 306 Godineau E, Schäfer C, Landais Y. Org. Lett. 2006; 8: 4871
    PubMed
  • 307 Gimazetdinov AM, Al’mukhametov AZ, Spirikhin LV, Miftakhov MS. Tetrahedron Lett. 2017; 58: 3242
  • 308 Yazici A, Wille U, Pyne SG. J. Org. Chem. 2016; 81: 1434
    PubMed
  • 309 Bauer A, Maulide N. Org. Lett. 2018; 20: 1461
    PubMed
  • 310 Hassan H, Pirenne V, Wissing M, Khiar C, Hussain A, Robert F, Landais Y. Chem.–Eur. J. 2017; 23: 4651
    PubMed
  • 311 Lühning LH, Strehl J, Schmidtmann M, Doye S. Chem.–Eur. J. 2017; 23: 4197
    PubMed
  • 312 Wang L, Seiders II JR, Floreancig PE. J. Am. Chem. Soc. 2004; 126: 12 596
  • 313 Kano N, Yamamura M, Kawashima T. J. Am. Chem. Soc. 2004; 126: 6250
    PubMed
  • 314 Yamamura M, Kano N, Kawashima T. J. Organomet. Chem. 2007; 692: 313
  • 315 Aouf C, Santelli M. Tetrahedron Lett. 2011; 52: 688
  • 316 Ogasawara M, Ge Y, Uetake K, Fan L, Takahashi T. J. Org. Chem. 2005; 70: 3871
    PubMed
  • 317 Leibeling M, Shurrush KA, Werner V, Perrin L, Marek I. Angew. Chem. Int. Ed. 2016; 55: 6057
    PubMed
  • 318 Kozuka M, Mitani M. J. Chem. Res. 2007; 464
  • 319 Rouquet G, Robert F, Méreau R, Castet F, Landais Y. Chem.–Eur. J. 2011; 17: 13 904
  • 320 Aoki K, Shimada T, Hayashi T. Tetrahedron: Asymmetry 2004; 15: 1771
  • 321 Tanaka N, Mizoshita N, Maegawa Y, Tani T, Inagaki S, Jorapur YR, Shimada T. Chem. Commun. (Cambridge) 2011; 47: 5025
    PubMed
  • 322 Wang Y, Hu S, Brittain WJ. Macromolecules 2006; 39: 5675
  • 323 Buckle MJC, Fleming I, Gil S, Pang KLC. Org. Biomol. Chem. 2004; 2: 749
    PubMed
  • 324 Noguchi N, Nakada M. Org. Lett. 2006; 8: 2039
    PubMed
  • 325 Hakamata H, Sato S, Ueda H, Tokuyama H. Org. Lett. 2017; 19: 5308
    PubMed
  • 326 Guo H, Mortensen MS, O’Doherty GA. Org. Lett. 2008; 10: 3149
    PubMed
  • 327 Son YW, Kwon TH, Lee JK, Pae AN, Lee JY, Cho YS, Min S.-J. Org. Lett. 2011; 13: 6500
    PubMed
  • 328 Keck GE, Kraft MB, Truong AP, Li W, Sanchez CC, Kedei N, Lewin NE, Blumberg PM. J. Am. Chem. Soc. 2008; 130: 6660
    PubMed
  • 329 Chabaud L, Landais Y, Renaud P. Org. Lett. 2005; 7: 2587
    PubMed
  • 330 Wijdeven MA, Wijtmans R, van den Berg RJF, Noorduin W, Schoemaker HE, Sonke T, van Delft FL, Blaauw RH, Fitch RW, Spande TF, Daly JW, Rutjes FPJT. Org. Lett. 2008; 10: 4001
    PubMed
  • 331 Huang H, Panek JS. Org. Lett. 2003; 5: 1991
    PubMed