Asymmetric Cyclopropanation Reactions

Abstract

Both physical and organic chemists are interested in the cyclopropane ring, the former owing to the strain inherent to the small ring structure, the latter prompted by the importance of this ring in naturally occurring compounds. In recent years, the increasing interest in enantioselective organic synthesis has led to a large number of papers on the preparation of cyclopropane compounds in enantioenriched form. The last review on asymmetric cyclopropanation reactions is dated 2008, thus an update is necessary with critical comparison of preparations using chiral auxiliaries, chiral metal complexes and organocatalysts. The aim of this review is an overview of these topics from 2008 to mid-2013.

1 Introduction

2 Simmons–Smith Cyclopropanation

2.1 Chiral Auxiliaries

2.2 Chiral Catalysts

3 Transition-Metal-Catalyzed Decomposition of Diazoalkanes

3.1 Cobalt

3.2 Copper

3.3 Rhodium

3.4 Ruthenium

3.5 Other Metals

4 Michael-Initiated Ring Closure (MIRC)

4.1 Chiral Auxiliaries

4.2 Organocatalysis

4.3 Metal Catalysis

5 Miscellaneous

5.1 C–H Insertion

5.2 Nucleophilic Ring Closure

5.3 Cycloisomerization of 1,n-Enynes

5.4 Other Methods

6 Conclusion

7 Abbreviations

Key words

cyclization - asymmetric synthesis - metal catalysis - enantioselectivity - carbenoids

• References

• 1a Topics in Current Chemistry . Vol. 133. De Meijere A. Springer; Heidelberg: 1986
• 1b The Chemistry of the Cyclopropyl Group . Rappoport Z, Patai S. John Wiley & Sons Ltd; New York: 1987
• 1c The Chemistry of the Cyclopropyl Group . Vol. 2. Rappoport Z, Patai S. John Wiley & Sons Ltd; New York: 1995
• 1d Topics in Current Chemistry . Vol. 135. De Meijere A. Springer; Heidelberg: 1987
• 1e Topics in Current Chemistry . Vol. 144. De Meijere A. Springer; Heidelberg: 1988
• 1f Topics in Current Chemistry . Vol. 155. De Meijere A. Springer; Heidelberg: 1990
• 1g Topics in Current Chemistry . Vol. 178. De Meijere A. Springer; Heidelberg: 1996
• 1h Houben-Weyl: Carbocyclic Three and Four-Membered Ring Compounds . Vol. E17a-c. De Meijere A. Thieme; Stuttgart: 1997
• 1i Topics in Current Chemistry . Vol. 207. De Meijere A. Springer; Berlin: 2000
• 2a de Meijere A. Angew. Chem. Int. Ed. 1979; 18: 809
• 2b Wiberg KB. Structures, Energies and Spectra of Cyclopropanes. In Cyclopropyl Group . Vols. 1 and 2. Rappoport Z. John Wiley & Sons, Ltd; New York: 2005: 1
• 2c Goudreau SR, Charette AB. Angew. Chem. Int. Ed. 2010; 49: 486
• 3 Marek I, Simaan S, Masarwa A. Angew. Chem. Int. Ed. 2007; 46: 7364
• 4a Salaun J, Baird MS. Curr. Med. Chem. 1995; 2: 511
• 4b Salaun J. Topics in Current Chemistry. Vol. 207. de Meijere A. Springer; Heidelberg: 2000: 1
• 4c Gnad F, Reiser O. Chem. Rev. 2003; 103: 1603
• 4d Wessjohann LA, Brandt W, Thiemann T. Chem. Rev. 2003; 103: 1625
• 4e Brackmann F, de Meijere A. Chem. Rev. 2007; 107: 4493
• 4f Brackmann F, de Meijere A. Chem. Rev. 2007; 107: 4538
• 5 Thibodeaux CJ, Chang W.-c, Liu H.-w. Chem. Rev. 2012; 112: 1681
• 6a Liu H.-W, Walsh CT In Cyclopropyl Group . Vols. 1 and 2. Rappoport Z. John Wiley & Sons Ltd; New York: 2005: 959
• 6b Gagnon A, Duplessis M, Fader L. Org. Prep. Proced. Int. 2010; 42: 1
• 7 Charette AB, Beauchemin A. Simmons-Smith Cyclopropanation Reaction. In Organic Reactions . Vol. 58. Overmann LE. John Wiley & Sons Ltd; New York: 2001: 1
• 8 Davies HM. L, Antoulinakis EG. Intermolecular Metal-Catalyzed Carbenoid Cyclopropanations. In Organic Reactions . Overmann LE. John Wiley & Sons Ltd; New York: 2001: 1
• 9 Little RD, Dawson JR. Tetrahedron Lett. 1980; 21: 2609
• 10 Lebel H, Marcoux J.-F, Molinaro C, Charette AB. Chem. Rev. 2003; 103: 977
• 11 Pellissier H. Tetrahedron 2008; 64: 7041
• 12a Sun X.-L, Tang Y. Acc. Chem. Res. 2008; 41: 937
• 12b Caballero A, Prieto A, Díaz-Requejo MM, Pérez PJ. Eur. J. Inorg. Chem. 2009; 1137
• 12c Audran G, Pellissier H. Adv. Synth. Catal. 2010; 352: 575
• 12d Intrieri D, Caselli A, Gallo E. Eur. J. Inorg. Chem. 2011; 5071
• 12e Zhang D, Song H, Qin Y. Acc. Chem. Res. 2011; 44: 447
• 12f Zhu S, Cui X, Zhang XP. Eur. J. Inorg. Chem. 2012; 430
• 12g David E, Milanole G, Ivashkin P, Couve-Bonnaire S, Jubault P, Pannecoucke X. Chem. Eur. J. 2012; 18: 14904
• 12h Kim HY, Walsh PJ. Acc. Chem. Res. 2012; 45: 1533
• 13 Honma M, Takeda H, Takano M, Nakada M. Synlett 2009; 1695
• 14 Simmons HE, Smith RD. J. Am. Chem. Soc. 1958; 80: 5323
• 15 Cornwall RG, Wong OA, Du H, Ramirez TA, Shi Y. Org. Biomol. Chem. 2012; 10: 5498
• 16 Chan JH. H, Rickborn B. J. Am. Chem. Soc. 1968; 90: 6406
• 17 Vega-Pérez JM, Perinan I, Vega M, Iglesias-Guerra F. Tetrahedron: Asymmetry 2008; 19: 1720
• 18 Vega-Pèrez JM, Perinàn I, Iglesias-Guerra F. Tetrahedron: Asymmetry 2009; 20: 1065
• 19 Vega-Pérez JM, Perinan I, Palo-Nieto C, Vega-Holm M, Iglesias-Guerra F. Tetrahedron: Asymmetry 2010; 21: 81
• 20 Lu T, Hayashi R, Hsung RP, DeKorver KA, Lohse AG, Song Z, Tang Y. Org. Biomol. Chem. 2009; 7: 3331
• 21 Song Z, Lu T, Hsung RP, Al-Rashid ZF, Ko C, Tang Y. Angew. Chem. Int. Ed. 2007; 46: 4069
• 22 Cheeseman M, Davies IR, Axe P, Johnson AL, Bull SD. Org. Biomol. Chem. 2009; 7: 3537
• 23 Ko K.-Y, Yun H.-S. Bull. Korean Chem. Soc. 2012; 33: 2415
• 24 Charette AB, Juteau H. J. Am. Chem. Soc. 1994; 116: 2651
• 25 Wang T, Liang Y, Yu Z.-X. J. Am. Chem. Soc. 2011; 133: 9343
• 26 Charette AB, Gagnon A, Fournier J.-F. J. Am. Chem. Soc. 2001; 124: 386
• 27 Zimmer LE, Charette AB. J. Am. Chem. Soc. 2009; 131: 15624
• 28 Beaulieu L.-PB, Zimmer LE, Charette AB. Chem. Eur. J. 2009; 15: 11829
• 29 Beaulieu L.-PB, Zimmer LE, Gagnon A, Charette AB. Chem. Eur. J. 2012; 18: 14784
• 30 Goudreau SR, Charette AB. J. Am. Chem. Soc. 2009; 131: 15633
• 31 Anthes R, Benoit S, Chen C.-K, Corbett EA, Corbett RM, DelMonte AJ, Gingras S, Livingston RC, Pendri Y, Sausker J, Soumeillant M. Org. Process Res. Dev. 2008; 12: 178
• 32 Kim HY, Salvi L, Carroll PJ, Walsh PJ. J. Am. Chem. Soc. 2009; 131: 954
• 33 Kim HY, Salvi L, Carroll PJ, Walsh PJ. J. Am. Chem. Soc. 2010; 132: 402
• 34 Valenta P, Carroll PJ, Walsh PJ. J. Am. Chem. Soc. 2010; 132: 14179
• 35 Kim HY, Lurain AE, Garcia-Garcia P, Carroll PJ, Walsh PJ. J. Am. Chem. Soc. 2005; 127: 13138
• 36 Kim HY, Walsh PJ. J. Phys. Org. Chem. 2012; 25: 933
• 37a Long J, Yuan Y, Shi Y. J. Am. Chem. Soc. 2003; 125: 13632
• 37b Long J, Du H, Li K, Shi Y. Tetrahedron Lett. 2005; 46: 2737
• 37c Du H, Long J, Shi Y. Org. Lett. 2006; 8: 2827
• 38 Long J, Xu L, Du H, Li K, Shi Y. Org. Lett. 2009; 11: 5226
• 39 Zheng Y, Zhang J. Adv. Synth. Catal. 2010; 352: 1810
• 40 Nakamura M, Hirai A, Nakamura E. J. Am. Chem. Soc. 2003; 125: 2341
• 41 Shitama H, Katsuki T. Angew. Chem. Int. Ed. 2008; 47: 2450
• 42 Xiao-hua S, Cun L, Zhao J, Cai-rong Z, Deng-gao J. J. Chem. Res. 2011; 35: 582
• 43 Nozaki H, Moriuti S, Takaya H, Noyori R. Tetrahedron Lett. 1966; 7: 5239
• 44 Doyle MP. Angew. Chem. Int. Ed. 2009; 48: 850
• 45 Dzik WI, Xu X, Zhang XP, Reek JN. H, de Bruin B. J. Am. Chem. Soc. 2010; 132: 10891
• 46 Lu H, Dzik WI, Xu X, Wojtas L, de Bruin B, Zhang XP. J. Am. Chem. Soc. 2011; 133: 8518
• 47 Fantauzzi S, Gallo E, Rose E, Raoul N, Caselli A, Issa S, Ragaini F, Cenini S. Organometallics 2008; 27: 6143
• 48 Belof JL, Cioce CR, Xu X, Zhang XP, Space B, Woodcock HL. Organometallics 2011; 30: 2739
• 49 Zhu S, Perman JA, Zhang XP. Angew. Chem. Int. Ed. 2008; 47: 8460
• 50 Charette AB, Wurz R. J. Mol. Catal. A: Chem. 2003; 196: 83
• 51 Ruppel JV, Gauthier TJ, Snyder NL, Perman JA, Zhang XP. Org. Lett. 2009; 11: 2273
• 52 Zhu S, Ruppel JV, Lu H, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2008; 130: 5042
• 53 Zhu S, Xu X, Perman JA, Zhang XP. J. Am. Chem. Soc. 2010; 132: 12796
• 54 Xu X, Lu H, Ruppel JV, Cui X, Lopez de Mesa S, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2011; 133: 15292
• 55 Langlotz BK, Wadepohl H, Gade LH. Angew. Chem. Int. Ed. 2008; 47: 4670
• 56 Koehn SK, Gronert S, Aldajaei JT. Org. Lett. 2010; 12: 676
• 57 Morandi B, Mariampillai B, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 1101
• 58 Evans DA, Woerpel KA, Hinman MM, Faul MM. J. Am. Chem. Soc. 1991; 113: 726
• 59 Drudis-Solé G, Maseras F, Lledós A, Vallribera A, Moreno-Mañas M. Eur. J. Org. Chem. 2008; 5614
• 60 Aguado-Ullate S, Urbano-Cuadrado M, Villalba I, Pires E, García JI, Bo C, Carbó JJ. Chem. Eur. J. 2012; 18: 14026
• 61 Minuth T, Boysen MM. K. Synthesis 2010; 2799
• 62 Ozoduru G, Schubach T, Boysen MM. K. Org. Lett. 2012; 14: 4990
• 63 Gök Y, Van der Eycken J. Helv. Chim. Acta 2012; 95: 831
• 64a Hirai S, Nakada M. Tetrahedron Lett. 2010; 51: 5076
• 64b Hirai S, Nakada M. Tetrahedron 2011; 67: 518
• 65 Chen S, Rong C, Feng P, Li S, Shi Y. Org. Biomol. Chem. 2012; 10: 5518
• 66 Moreau B, Alberico D, Lindsay VN. G, Charette AB. Tetrahedron 2012; 68: 3487
• 67 Sawada T, Nakada M. Tetrahedron: Asymmetry 2012; 23: 350
• 68 Sawada T, Nakada M. Org. Lett. 2013; 15: 1004
• 69 Suárez del Villar I, Gradillas A, Pérez-Castells J. Eur. J. Org. Chem. 2010; 5850
• 70 Mandoli A, Garzelli R, Orlandi S, Pini D, Lessi M, Salvadori P. Catal. Today 2009; 140: 51
• 71 Carreiro EP, Moura NM. M, Burke AJ. Eur. J. Org. Chem. 2012; 518
• 72 Silva AR, Albuquerque H, Borges S, Siegel R, Mafra L, Carvalho AP, Pires J. Microporous Mesoporous Mater. 2012; 158: 26
• 73 Carreiro EP, Burke AJ, Ramalho JP. P, Rodrigues AI. Tetrahedron: Asymmetry 2009; 20: 1272
• 74 Carreiro EP, Ramalho JP. P, Burke AJ. Tetrahedron 2011; 67: 4640
• 75 Caselli A, Cesana F, Gallo E, Casati N, Macchi P, Sisti M, Celentano G, Cenini S. Dalton Trans. 2008; 4202
• 76 Castano B, Guidone S, Gallo E, Ragaini F, Casati N, Macchi P, Sisti M, Caselli A. Dalton Trans. 2013; 42: 2451
• 77 Lee W.-S, Yeung C.-T, Sham K.-C, Wong W.-T, Kwong H.-L. Polyhedron 2011; 30: 178
• 78 Mloston G, Mucha P, Heimgartner H. Lett. Org. Chem. 2012; 9: 89
• 79 Biegasiewicz KF, Ingalsbe ML, Denis JD. S, Gleason JL, Ho J, Coote ML, Savage GP, Priefer R. Beilstein J. Org. Chem. 2012; 8: 1814
• 80 Masterson DS, Shirley C, Glatzhofer DT. J. Mol. Catal. A: Chem. 2012; 361-362: 111
• 81 Pelphrey P, Hansen J, Davies HM. L. Chem. Sci. 2010; 1: 254
• 82 DeAngelis A, Dmitrenko O, Yap GP. A, Fox JM. J. Am. Chem. Soc. 2009; 131: 7230
• 83 Lindsay VN. G, Lin W, Charette AB. J. Am. Chem. Soc. 2009; 131: 16383
• 84 Lindsay VN. G, Nicolas C, Charette AB. J. Am. Chem. Soc. 2011; 133: 8972
• 85 Awata A, Arai T. Synlett 2013; 24: 29
• 86 Goto T, Takeda K, Anada M, Ando K, Hashimoto S. Tetrahedron Lett. 2011; 52: 4200
• 87 Lindsay VN. G, Charette AB. ACS Catalysis 2012; 2: 1221
• 88 Boruta DT, Dmitrenko O, Yap GP. A, Fox JM. Chem. Sci. 2012; 3: 1589
• 89 Panne P, DeAngelis A, Fox JM. Org. Lett. 2008; 10: 2987
• 90 Goto T, Takeda K, Shimada N, Nambu H, Anada M, Shiro M, Ando K, Hashimoto S. Angew. Chem. Int. Ed. 2011; 50: 6803
• 91 Ghanem A, Gardiner MG, Williamson RM, Müller P. Chem. Eur. J. 2010; 16: 3291
• 92 Marcoux D, Charette AB. Angew. Chem. Int. Ed. 2008; 47: 10155
• 93 Marcoux D, Goudreau SR, Charette AB. J. Org. Chem. 2009; 74: 8939
• 94 Marcoux D, Lindsay VN. G, Charette AB. Chem. Commun. 2010; 46: 910
• 95 Marcoux D, Azzi S, Charette AB. J. Am. Chem. Soc. 2009; 131: 6970
• 96 Chuprakov S, Kwok SW, Zhang L, Lercher L, Fokin VV. J. Am. Chem. Soc. 2009; 131: 18034
• 97 Grimster N, Zhang L, Fokin VV. J. Am. Chem. Soc. 2010; 132: 2510
• 98 Ventura DL, Li Z, Coleman MG, Davies HM. L. Tetrahedron 2009; 65: 3052
• 99 Nadeau E, Ventura DL, Brekan JA, Davies HM. L. J. Org. Chem. 2010; 75: 1927
• 100 Watanabe N, Ohtake Y, Hashimoto S.-i, Shiro M, Ikegami S. Tetrahedron Lett. 1995; 36: 1491
• 101 Denton JR, Cheng K, Davies HM. L. Chem. Commun. 2008; 1238
• 102 Denton JR, Davies HM. L. Org. Lett. 2009; 11: 787
• 103 McMills MC, Humes RJ, Pavlyuk OM. Tetrahedron Lett. 2012; 53: 849
• 104 Melby T, Hughes RA, Hansen T. Synlett 2007; 2277
• 105 Gu P, Su Y, Wu X.-P, Sun J, Liu W, Xue P, Li R. Org. Lett. 2012; 14: 2246
• 106 Bonge HT, Kaboli M, Hansen T. Tetrahedron Lett. 2010; 51: 5375
• 107 Lindsay VN. G, Fiset D, Gritsch PJ, Azzi S, Charette AB. J. Am. Chem. Soc. 2013; 135: 1463
• 108 Qin C, Boyarskikh V, Hansen JH, Hardcastle KI, Musaev DG, Davies HM. L. J. Am. Chem. Soc. 2011; 133: 19198
• 109 Sambasivan R, Ball ZT. Angew. Chem. Int. Ed. 2012; 51: 8568
• 110 Nishimura T, Maeda Y, Hayashi T. Angew. Chem. Int. Ed. 2010; 49: 7324
• 111 Grabulosa A, Mannu A, Mezzetti A, Muller G. J. Organomet. Chem. 2012; 696: 4221
• 112 Ito J.-i, Ujiie S, Nishiyama H. Chem. Eur. J. 2010; 16: 4986
• 113 Xu Z.-J, Fang R, Zhao C, Huang J.-S, Li G.-Y, Zhu N, Che C.-M. J. Am. Chem. Soc. 2009; 131: 4405
• 114 Gill CS, Venkatasubbaiah K, Jones CW. Adv. Synth. Catal. 2009; 351: 1344
• 115 Falkowski JM, Liu S, Wang C, Lin W. Chem. Commun. 2012; 48: 6508
• 116 del Pozo C, Corma A, Iglesias M, Sanchez F. Green Chem. 2011; 13: 2471
• 117 Chanthamath S, Phomkeona K, Shibatomi K, Iwasa S. Chem. Commun. 2012; 48: 7750
• 118 Chanthamath S, Nguyen DT, Shibatomi K, Iwasa S. Org. Lett. 2013; 15: 772
• 119 Abu-Elfotoh A.-M, Nguyen DP. T, Chanthamath S, Phomkeona K, Shibatomi K, Iwasa S. Adv. Synth. Catal. 2012; 354: 3435
• 120 Abu-Elfotoh A.-M, Phomkeona K, Shibatomi K, Iwasa S. Angew. Chem. Int. Ed. 2010; 49: 8439
• 121 Yeung C.-T, Lee W.-S, Tsang C.-S, Yiu S.-M, Wong W.-T, Wong W.-Y, Kwong H.-L. Polyhedron 2010; 29: 1497
• 122 Suematsu H, Kanchiku S, Uchida T, Katsuki T. J. Am. Chem. Soc. 2008; 130: 10327
• 123 Ichinose M, Suematsu H, Katsuki T. Angew. Chem. Int. Ed. 2009; 48: 3121
• 124 Cao Z.-Y, Zhou F, Yu Y.-H, Zhou J. Org. Lett. 2013; 15: 42
• 125 Ty N, Pontikis R, Chabot GG, Devillers E, Quentin L, Bourg S, Florent J.-C. Bioorg. Med. Chem. 2013; 21: 1357
• 126a Topics in Current Chemistry. Vol. 291. List B. Springer; Heidelberg: 2009
• 126b Piovesana S, Schietroma DM. S, Bella M. Angew. Chem. Int. Ed. 2011; 50: 6216
• 126c Moyano A, Rios R. Chem. Rev. 2011; 111: 4703
• 126d Rueping M, Kuenkel A, Atodiresei I. Chem. Soc. Rev. 2011; 40: 4539
• 126e Cheong PH.-Y, Legault CY, Um JM, Celebi-Oelcuem N, Houk KN. Chem. Rev. 2011; 111: 5042
• 127 Shen X, Zhang W, Zhang L, Luo T, Wan X, Gu Y, Hu J. Angew. Chem. Int. Ed. 2012; 51: 6966
• 128 Wang H.-Y, Yang F, Li X.-L, Yan X.-M, Huang Z.-Z. Chem. Eur. J. 2009; 15: 3784
• 129 Zhou R, Deng X, Zheng J, Sheng Q, Sun X, Tang Y. Chin. J. Chem. 2011; 29: 995
• 130 Zhu B.-H, Zhou R, Zheng J.-C, Deng X.-M, Sun X.-L, Shen Q, Tang Y. J. Org. Chem. 2010; 75: 3454
• 131 Riches SL, Saha C, Filgueira NF, Grange E, McGarrigle EM, Aggarwal VK. J. Am. Chem. Soc. 2010; 132: 7626
• 132 Kanomata N, Sakaguchi R, Sekine K, Yamashita S, Tanaka H. Adv. Synth. Catal. 2010; 352: 2966
• 133 Abramovitch A, Fensterbank L, Malacria M, Marek I. Angew. Chem. Int. Ed. 2008; 47: 6865
• 134 Palko JW, Buist PH, Manthorpe JM. Tetrahedron: Asymmetry 2013; 24: 165
• 135 Midura WH, Krysiak J, Rzewnicka A, Supel A, Lizwa P, Ewas AM. Tetrahedron 2013; 69: 730
• 136 Ivashkin P, Couve-Bonnaire S, Jubault P, Pannecoucke X. Org. Lett. 2012; 14: 5130
• 137 Atta AK, Pathak T. J. Org. Chem. 2009; 74: 2710
• 138 Biswas A, De Sarkar S, Tebben L, Studer A. Chem. Commun. 2012; 48: 5190
• 139 Cheng Y, An J, Lu L.-Q, Luo L, Wang Z.-Y, Chen J.-R, Xiao W.-J. J. Org. Chem. 2011; 76: 281
• 140 Wang J, Liu X, Dong S, Lin L, Feng X. J. Org. Chem. 2013; 78: 6322
• 141 Gao L, Hwang G.-S, Ryu DH. J. Am. Chem. Soc. 2011; 133: 20708
• 142 Vesely J, Zhao G.-L, Bartoszewicz A, Còrdova A. Tetrahedron Lett. 2008; 49: 4209
• 143 Zhang J.-m, Hu Z.-p, Dong L.-t, Xuan Y.-n, Lou C.-L, Yan M. Tetrahedron: Asymmetry 2009; 20: 355
• 144 Inokuma T, Sakamoto S, Takemoto Y. Synlett 2009; 1627
• 145 Wascholowski V, Hansen HM, Longbottom DA, Ley SV. Synthesis 2008; 1269
• 146 Lv J, Zhang J, Lin Z, Wang Y. Chem. Eur. J. 2009; 15: 972
• 147 Dong L.-t, Du Q.-s, Lou C.-l, Zhang J.-m, Lu R.-j, Yan M. Synlett 2010; 266
• 148 Pesciaioli F, Righi P, Mazzanti A, Bartoli G, Bencivenni G. Chem. Eur. J. 2011; 17: 2842
• 149 Dou X, Lu Y. Chem. Eur. J. 2012; 18: 8315
• 150 Das U, Tsai Y.-L, Lin W. Org. Biomol. Chem. 2013; 11: 44
• 151 Fan R, Ye Y, Li W, Wang L. Adv. Synth. Catal. 2008; 350: 2488
• 152 Xuan Y.-n, Nie S.-z, Dong L.-t, Zhang J.-m, Yan M. Org. Lett. 2009; 11: 1583
• 153 Russo A, Lattanzi A. Tetrahedron: Asymmetry 2010; 21: 1155
• 154 Noole A, Sucman NS, Kabeshov MA, Kanger T, Macaev FZ, Malkov AV. Chem. Eur. J. 2012; 18: 14929
• 155 Ibrahem I, Zhao G.-L, Rios R, Vesely J, Sundén H, Dziedzic P, Córdova A. Chem. Eur. J. 2008; 14: 7867
• 156 Companyó X, Alba A.-N, Cárdenas F, Moyano A, Rios R. Eur. J. Org. Chem. 2009; 3075
• 157 Uria U, Vicario JL, Badìa D, Carrillo L, Reyes E, Pesquera A. Synthesis 2010; 701
• 158 Terrasson V, van der Lee A, Marcia de Figueiredo R, Campagne JM. Chem. Eur. J. 2010; 16: 7875
• 159 Del Fiandra C, Piras L, Fini F, Disetti P, Moccia M, Adamo MF. A. Chem. Commun. 2012; 48: 3863
• 160 Russo A, Meninno S, Tedesco C, Lattanzi A. Eur. J. Org. Chem. 2011; 5096
• 161 Rueping M, Sunden H, Hubener L, Sugiono E. Chem. Commun. 2012; 48: 2201
• 162 Herchl R, Waser M. Tetrahedron Lett. 2013; 54: 2472
• 163 Li W, Li X, Ye T, Wu W, Liang X, Ye J. Tetrahedron Lett. 2011; 52: 2715
• 164 Noole A, Oseka M, Pehk T, Oeren M, Jarving I, Elsegood MR. J, Malkov AV, Lopp M, Kanger T. Adv. Synth. Catal. 2013; 355: 829
• 165 Russo A, Lattanzi A. Org. Biomol. Chem. 2011; 9: 7993
• 166 Marini F, Sternativo S, Del Verme F, Testaferri L, Tiecco M. Adv. Synth. Catal. 2009; 351: 1801
• 167 Kumaraswamy G, Padmaja M. J. Org. Chem. 2008; 73: 5198
• 168 Papageorgiou CD, Cubillo de Dios MA, Ley SV, Gaunt MJ. Angew. Chem. Int. Ed. 2004; 43: 4641
• 169 Kumaraswamy G, Ramakrishna G, Sridhar B. Tetrahedron Lett. 2011; 52: 1778
• 170 den Hartog T, Rudolph A, Macià B, Minnaard AJ, Feringa BL. J. Am. Chem. Soc. 2010; 132: 14349
• 171 Lee HJ, Kim SM, Kim DY. Tetrahedron Lett. 2012; 53: 3437
• 172 Ogata S, Saitoh H, Wakasugi D, Satoh T. Tetrahedron 2008; 64: 5711
• 173 Satoh T, Kuramoto T, Ogata S, Watanabe H, Saitou T, Tadokoro M. Tetrahedron: Asymmetry 2010; 21: 1
• 174 Kimura T, Hattori Y, Momochi H, Nakaya N, Satoh T. Synlett 2013; 24: 483
• 175 Clarke C, Foussat S, Fox DJ, Pedersen DS, Warren S. Org. Biomol. Chem. 2009; 7: 1323
• 176 Krawczyk H, Wasek K, Kedzia J. Synthesis 2009; 1473
• 177 Bray CD, Minicone F. Chem. Commun. 2010; 46: 5867
• 178a Singh AK, Rao MN, Simpson JH, Li W.-S, Thornton JE, Kuehner DE, Kacsur DJ. Org. Process Res. Dev. 2002; 6: 618
• 178b Delhaye L, Merschaert A, Delbeke P, Brione W. Org. Process Res. Dev. 2007; 11: 689
• 179 Robinson A, Aggarwal VK. Angew. Chem. Int. Ed. 2010; 49: 6673
• 180 Hardee DJ, Lambert TH. J. Am. Chem. Soc. 2009; 131: 7536
• 181 Winter P, Swatschek J, Willot M, Radtke L, Olbrisch T, Schafer A, Christmann M. Chem. Commun. 2011; 47: 12200
• 182 Alliot J, Gravel E, Pillon F, Buisson D.-A, Nicolas M, Doris E. Chem. Commun. 2012; 48: 8111
• 183 White JD, Lincoln CM, Yang J, Martin WH. C, Chan DB. J. Org. Chem. 2008; 73: 4139
• 184 Kallemeyn JM, Mulhern MM, Ku Y.-Y. Synlett 2011; 535
• 185 Ito H, Kosaka Y, Nonoyama K, Sasaki Y, Sawamura M. Angew. Chem. Int. Ed. 2008; 47: 7424
• 186 Pietruszka J, Solduga G. Eur. J. Org. Chem. 2009; 5998
• 187 Nishimura T, Kawamoto T, Nagaosa M, Kumamoto H, Hayashi T. Angew. Chem. Int. Ed. 2010; 49: 1638
• 188 Pradal A, Chao C.-M, Toullec PY, Michelet V. Beilstein J. Org. Chem. 2011; 7: 1021
• 189 Newcomb ET, Ferreira EM. Org. Lett. 2013; 15: 1772
• 190 Fürstner A, Schlecker A. Chem. Eur. J. 2008; 14: 9181
• 191 Watson ID. G, Ritter S, Toste FD. J. Am. Chem. Soc. 2009; 131: 2056
• 192 Soriano E, Marco-Contelles J. Chem. Eur. J. 2008; 14: 6771
• 193 Strand RB, Helgerud T, Solvang T, Dolva A, Sperger CA, Fiksdahl A. Tetrahedron: Asymmetry 2012; 23: 1350
• 194 Shibata Y, Noguchi K, Hirano M, Tanaka K. Org. Lett. 2008; 10: 2825
• 195 Cruz Cruz D, Yuste F, Martin MR, Tito A, Garcia Ruano JL. J. Org. Chem. 2009; 74: 3820
• 196a Ouizem S, Cheramy S, Botuha C, Chemla F, Ferreira F, Pérez-Luna A. Chem. Eur. J. 2010; 16: 12668
• 196b Ouizem S, Chemla F, Ferreira F, Perez-Luna A. Synlett 2012; 23: 1374
• 197 Lauru S, Simpkins NS, Gethin D, Wilson C. Chem. Commun. 2008; 5390
• 198 Chen DY. K, Pouwer RH, Richard J.-A. Chem. Soc. Rev. 2012; 41: 4631