Download PDF
Gao, S. et al.: 2016 Science of Synthesis, 2016/4b: Metal-Catalyzed Cyclization Reactions 2 DOI: 10.1055/sos-SD-222-00346
Metal-Catalyzed Cyclization Reactions 2

2.10 Ring-Closing Metathesis

More Information

Book

Editors: Gao, S.; Ma, S.

Authors: Bora, U.; Dominguez, G.; Du, H.; Garve, L.; Harmata, M.; Hu, W.; Jones, D. E.; Lee, D.; Li, X.; Mondal, M.; Pérez Castells, J.; Sabbasani, V. R.; Shibata, Y.; Tanaka, K.; Tang, W.; Werz, D. B.; Xia, F.; Xu, X.; Ye, S.

Title: Metal-Catalyzed Cyclization Reactions 2

Print ISBN: 9783131998118; Online ISBN: 9783132404823; Book DOI: 10.1055/b-004-129734

1st edition © 2016 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart

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

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

Also available at
 


Abstract

Ring-closing metathesis (RCM) has emerged as a powerful synthetic tool. Depending on the unsaturated functional groups involved, ring-closing-metathesis reactions are classified into three categories: diene ring-closing metathesis, enyne ring-closing metathesis, and diyne ring-closing metathesis. These are mediated/catalyzed by metal alkylidenes or alkylidynes to form cyclic alkenes or alkynes, with ring sizes ranging from small to large, and including both carbocycles and heterocycles. Mechanistically, diene and diyne ring-closing metathesis involves an exchange reaction between the participating alkenes or alkynes, whereas enyne ring-closing metathesis involves a formal addition reaction between an alkene and an alkyne. This chapter summarizes the distinctive features of these different ring-closing metathesis processes in terms of the advancement of mechanistic understanding and the development of effective catalyst systems and their application to natural product synthesis.

Key words

diene metathesis - diyne metathesis - enyne metathesis - ring-closing metathesis - ring rearrangement - ruthenium alkylidenes - metallotropic shift - molybdenum alkylidenes - molybdenum alkylidynes
 
  • 1 Villemin D. Tetrahedron Lett. 1980; 21: 1715
  • 2 Tsuji J, Hashiguchi S. Tetrahedron Lett. 1980; 21: 2955
  • 3 Fu GC, Grubbs RH. J. Am. Chem. Soc. 1993; 115: 3800
  • 4 Fu GC, Nguyen ST, Grubbs RH. J. Am. Chem. Soc. 1993; 115: 9856
  • 5 Katz TJ, Sivavec TM. Tetrahedron Lett. 1985; 26: 2159
  • 6 Katz TJ, Sivavec TM. J. Am. Chem. Soc. 1985; 107: 737
  • 7 Korkowski PF, Hoye TR, Rydberg DB. J. Am. Chem. Soc. 1988; 110: 2676
  • 8 Hoye TR, Rehberg GM. Organometallics 1989; 8: 2070
  • 9 Hoye TR, Rehberg GM. J. Am. Chem. Soc. 1990; 112: 2841
  • 10 Watanuki S, Ochifuji N, Mori M. Organometallics 1994; 13: 4129
  • 11 Watanuki S, Mori M. Organometallics 1995; 14: 5054
  • 12 Watanuki S, Ochifuji N, Mori M. Organometallics 1995; 14: 5062
  • 13 Kinoshita A, Mori M. Synlett 1994; 1020
  • 14 Kim S.-H, Bowden N, Grubbs RH. J. Am. Chem. Soc. 1994; 116: 10801
  • 15 Fürstner A, Seidel G. Angew. Chem. Int. Ed. 1998; 37: 1734
    PubMed
  • 16 Akiyama M, Chisholm MH, Cotton FA, Extine MW, Haitko DA, Little D, Fanwick PE. Inorg. Chem. 1979; 18: 2266
  • 17 Fürstner A, Guth O, Rumbo A, Seidel G. J. Am. Chem. Soc. 1999; 121: 11108
  • 18 Urbina-Blanco CA, Poater A, Lebl T, Manzini S, Slawin AMZ, Cavallo L, Nolan SP. J. Am. Chem. Soc. 2013; 135: 7073
    PubMed
  • 19 Romero PE, Piers WE, McDonald R. Angew. Chem. Int. Ed. 2004; 43: 6161
    PubMed
  • 20 van der Eide EF, Romero PE, Piers WE. J. Am. Chem. Soc. 2008; 130: 4485
    PubMed
  • 21 Schleyer PVR, Williams JE, Blanchard KR. J. Am. Chem. Soc. 1970; 92: 2378
  • 22 Bourgeois D, Pancrazi A, Ricard L, Prunet J. Angew. Chem. Int. Ed. 2000; 39: 725
    PubMed
  • 23 Matsui R, Seto K, Fujita K, Suzuki T, Nakazaki A, Kobayashi S. Angew. Chem. Int. Ed. 2010; 49: 10068
    PubMed
  • 24 Fürstner A, Radkowski K, Wirtz C, Goddard R, Lehmann CW, Mynott R. J. Am. Chem. Soc. 2002; 124: 7061
    PubMed
  • 25 Murga J, Falomir E, García-Fortanet J, Carda M, Marco JA. Org. Lett. 2002; 4: 3447
    PubMed
  • 26 Meng D, Su D.-S, Balog A, Bertinato P, Sorensen AJ, Danishefsky SJ, Zheng Y.-H, Chou T.-C, He L, Horwitz SB. J. Am. Chem. Soc. 1997; 119: 2733
  • 27 Fürstner A, Thiel OR, Blanda G. Org. Lett. 2000; 2: 3731
    PubMed
  • 28 Arisawa M, Kato C, Kaneko H, Nishida A, Nakagawa M. J. Chem. Soc., Perkin Trans. 1 2000; 1873
  • 29 Nakashima K, Ito R, Sono M, Tori M. Heterocycles 2000; 53: 301
  • 30 Lee CW, Grubbs RH. Org. Lett. 2000; 2: 2145
    PubMed
  • 31 Yu M, Wang C, Kyle AF, Jakubec P, Dixon DJ, Schrock RR, Hoveyda AH. Nature (London) 2011; 479: 88
  • 32 Wang Y, Jimenez M, Hansen AS, Raiber E.-A, Schreiber SL, Young DW. J. Am. Chem. Soc. 2011; 133: 9196
    PubMed
  • 33 Marx VM, Herbert MB, Keitz BK, Grubbs RH. J. Am. Chem. Soc. 2013; 135: 94
    PubMed
  • 34 Rosebrugh LE, Herbert MB, Marx VM, Keitz BK, Grubbs RH. J. Am. Chem. Soc. 2013; 135: 1276
    PubMed
  • 35 Quinn KJ, Isaacs AK, Arvary RA. Org. Lett. 2004; 6: 4143
    PubMed
  • 36 Quinn KJ, Isaacs AK, DeChristopher BA, Szklarz SC, Arvary RA. Org. Lett. 2005; 7: 1243
    PubMed
  • 37 Michaelis S, Blechert S. Org. Lett. 2005; 7: 5513
    PubMed
  • 38 Baylon C, Heck M.-P, Misoskowski C. J. Org. Chem. 1999; 64: 3354
    PubMed
  • 39 Heck M.-P, Baylon C, Nolan SP, Misoskowski C. Org. Lett. 2001; 3: 1989
    PubMed
  • 40 Clark JS, Hamelin O. Angew. Chem. Int. Ed. 2000; 39: 372
    PubMed
  • 41 Ma S, Ni B. Org. Lett. 2002; 4: 639
    PubMed
  • 42 Ma S, Ni B. Chem.–Eur. J. 2004; 10: 3286
    PubMed
  • 43 Sello JK, Andreana PR, Lee D, Schreiber SL. Org. Lett. 2003; 5: 4125
    PubMed
  • 44 Hoye TR, Jeffrey CS, Tennakoon MA, Wang J, Zhao H. J. Am. Chem. Soc. 2004; 126: 10210
    PubMed
  • 45 Hansen EC, Lee D. Org. Lett. 2004; 6: 2035
    PubMed
  • 46 Hansen Ph.D. EC. Thesis. University of Wisconsin; Madison, WI 2006
    Google Scholar
  • 47 Wang X, Bowman EJ, Bowman BJ, Porco Jr. JA. Angew. Chem. Int. Ed. 2004; 43: 3601
    PubMed
  • 48 Huwe CM, Velder J, Blechert S. Angew. Chem. Int. Ed. 1996; 35: 2376
  • 49 Huwe CM, Blechert S. Synthesis 1997; 61
  • 50 Evans PA, Cui J, Buffone GP. Angew. Chem. Int. Ed. 2003; 42: 1734
    PubMed
  • 51 Alexander JB, La DS, Cefalo DR, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 1998; 120: 4041
  • 52 La DS, Alexander JB, Cefalo DR, Graf DD, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 1998; 120: 9720
  • 53 Seiders TJ, Ward DW, Grubbs RH. Org. Lett. 2001; 3: 3225
    PubMed
  • 54 Zhu SS, Cefalo DR, La DS, Jamieson JY, Davis WM, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 1999; 121: 8251
  • 55 Funk TW, Berlin JM, Grubbs RH. J. Am. Chem. Soc. 2006; 128: 1840
    PubMed
  • 56 Sattely ES, Cortez GA, Moebius DC, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2005; 127: 8526
    PubMed
  • 57 Malcolmson SJ, Meek SJ, Sattely ES, Schrock RR, Hoveyda AH. Nature (London) 2008; 456: 933
  • 58 Donohoe TJ, Rosa CP. Org. Lett. 2007; 9: 5509
    PubMed
  • 59 Miller AK, Hughes CC, Kennedy-Smith JJ, Gradl SN, Trauner D. J. Am. Chem. Soc. 2006; 128: 17057
    PubMed
  • 60 Dai M, Danishefsky SJ. J. Am. Chem. Soc. 2007; 129: 3498
    PubMed
  • 61 Dai M, Krauss IJ, Danishefsky SJ. J. Org. Chem. 2008; 73: 9576
    PubMed
  • 62 Ziegler FE, Metcalf III CA, Nangia A, Schulte G. J. Am. Chem. Soc. 1993; 115: 2581
  • 63 Hanessian S, Margarita R, Hall A, Johnstone S, Tremblay M, Parlanti L. J. Am. Chem. Soc. 2002; 124: 13342
    PubMed
  • 64 Hanessian S, Tremblay M, Petersen JFW. J. Am. Chem. Soc. 2004; 126: 6064
    PubMed
  • 65 Trost BM, Horne DB, Woltering MJ. Angew. Chem. Int. Ed. 2003; 42: 5987
    PubMed
  • 66 Trost BM, Horne DB, Woltering MJ. Chem.–Eur. J. 2006; 12: 6607
    PubMed
  • 67 Crimmins MT, Zhang Y, Diaz FA. Org. Lett. 2006; 8: 2369
    PubMed
  • 68 She Ph.D. J. Dissertation, University of North Carolina at Chapel Hill. Chapel Hill; NC 2004
    Google Scholar
  • 69 Kuramochi A, Usuda H, Yamatsugu K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2005; 127: 14200
    PubMed
  • 70 Nicolaou KC, Tria GS, Edmonds DJ. Angew. Chem. Int. Ed. 2008; 47: 1780
    PubMed
  • 71 Hayashida J, Rawal VH. Angew. Chem. Int. Ed. 2008; 47: 4373
    PubMed
  • 72 Yun SY, Zheng J.-C, Lee D. Angew. Chem. Int. Ed. 2008; 47: 6201
    PubMed
  • 73 Tiefenbacher K, Mulzer J. J. Org. Chem. 2009; 74: 2937
    PubMed
  • 74 White DE, Stewart IC, Grubbs RH, Stoltz BM. J. Am. Chem. Soc. 2008; 130: 810
    PubMed
  • 75 Hoshi M, Kaneko O, Nakajima M, Arai S, Nishida A. Org. Lett. 2014; 16: 768
    PubMed
  • 76 Nagatomo M, Koshimizu M, Masuda K, Tabuchi T, Urabe D, Inoue M. J. Am. Chem. Soc. 2014; 136: 5916
    PubMed
  • 77 Zhang H, Curran DP. J. Am. Chem. Soc. 2011; 133: 10376
    PubMed
  • 78 Umezaki S, Yokoshima S, Fukuyama T. Org. Lett. 2013; 15: 4230
    PubMed
  • 79 Liu G, Romo D. Angew. Chem. Int. Ed. 2011; 50: 7537
    PubMed
  • 80 Nickel A, Maruyama T, Tang H, Murphy PD, Greene B, Yusuff N, Wood JL. J. Am. Chem. Soc. 2004; 126: 16300
    PubMed
  • 81 Watanabe K, Suzuki Y, Aoki K, Sakakura A, Suenaga K, Kigoshi H. J. Org. Chem. 2004; 69: 7802
    PubMed
  • 82 Ohyoshi T, Funakubo S, Miyazawa Y, Niida K, Hayakawa I, Kigoshi H. Angew. Chem. Int. Ed. 2012; 51: 4972
    PubMed
  • 83 Winkler JD, Rouse MB, Greaney MF, Harrison SJ, Jeon YT. J. Am. Chem. Soc. 2002; 124: 9726
    PubMed
  • 84 Kalidindi S, Jeong WB, Schall A, Bandichhor R, Nosse B, Reiser O. Angew. Chem. Int. Ed. 2007; 46: 6361
    PubMed
  • 85 Willot M, Radtke L, Könning D, Fröhlich R, Gessner VH, Strohmann C, Christmann M. Angew. Chem. Int. Ed. 2009; 48: 9105
    PubMed
  • 86 Zahel M, Keβberg A, Metz P. Angew. Chem. Int. Ed. 2013; 52: 5390
    PubMed
  • 87 Nicolaou KC, Bunnage ME, Koide K. J. Am. Chem. Soc. 1994; 116: 8402
  • 88 Cook GR, Shanker PS, Peterson SL. Org. Lett. 1999; 1: 615
    PubMed
  • 89 Fürstner A, Thiel OR. J. Org. Chem. 2000; 65: 1738
    PubMed
  • 90 Paquette LA, Tae J, Arrington MP, Sadoun AH. J. Am. Chem. Soc. 2000; 122: 2742
  • 91 Krafft ME, Cheung Y.-Y, Juliano-Capucao CA. Synthesis 2000; 1020
  • 92 Krafft ME, Cheung YY, Abboud KA. J. Org. Chem. 2001; 66: 7443
    PubMed
  • 93 Tsuna K, Noguchi N, Nakada M. Angew. Chem. Int. Ed. 2011; 50: 9452
    PubMed
  • 94 Hog DT, Huber FME, Mayer P, Trauner D. Angew. Chem. Int. Ed. 2014; 53: 8513
    PubMed
  • 95 Takao K.-I, Watanabe G, Yasui H, Tadano K.-I. Org. Lett. 2002; 4: 2941
    PubMed
  • 96 Crimmins MT, Choy AL. J. Am. Chem. Soc. 1999; 121: 5653
  • 97 Burton JW, Clark JS, Derrer S, Stork TC, Bendall JG, Holmes AB. J. Am. Chem. Soc. 1997; 119: 7483
  • 98 Crimmins MT, Emmitte KA. Org. Lett. 1999; 1: 2029
    PubMed
  • 99 Adsool VA, Pansare SV. Org. Biomol. Chem. 2008; 6: 2011
    PubMed
  • 100 Bratz M, Bullock WH, Overman LE, Takemoto T. J. Am. Chem. Soc. 1995; 117: 5958
  • 101 Matsui R, Seto K, Sato Y, Suzuki T, Nakazaki A, Kobayashi S. Angew. Chem. Int. Ed. 2011; 50: 680
    PubMed
  • 102 Volchkov I, Lee D. J. Am. Chem. Soc. 2013; 135: 5324
    PubMed
  • 103 Crimmins MT, Brown BH. J. Am. Chem. Soc. 2004; 126: 10264
    PubMed
  • 104 Larrosa I, Da Silva MI, Gómez PM, Hannen P, Ko E, Lenger SR, Linke SR, White AJP, Wilton D, Barrett AGM. J. Am. Chem. Soc. 2006; 128: 14042
    PubMed
  • 105 Lv L, Shen B, Li Z. Angew. Chem. Int. Ed. 2014; 53: 4164
    PubMed
  • 106 Brown MK, Hoveyda AH. J. Am. Chem. Soc. 2008; 130: 12904
    PubMed
  • 107 Cai Z, Yongpruksa N, Harmata M. Org. Lett. 2012; 14: 1661
    PubMed
  • 108 Kusuma BR, Brandt GEL, Blagg SJ. Org. Lett. 2012; 14: 6242
    PubMed
  • 109 Kurata K, Taniguchi K, Shiraishi K, Hayama N, Tanaka I, Suzuki M. Chem. Lett. 1989; 267
  • 110 Becker J, Butt L, von Kiedrowski V, Mischler E, Quentin F, Hiersemann M. Org. Lett. 2013; 15: 5982
    PubMed
  • 111 Gallenkamp D, Fürstner A. J. Am. Chem. Soc. 2011; 133: 9232
    PubMed
  • 112 Micoine K, Fürstner A. J. Am. Chem. Soc. 2010; 132: 14064
    PubMed
  • 113 Bali AK, Sunnam SK, Prasad KR. Org. Lett. 2014; 16: 4001
    PubMed
  • 114 Toelle N, Weinstabl H, Gaich T, Mulzer J. Angew. Chem. Int. Ed. 2014; 53: 3859
    PubMed
  • 115 Yun SY, Hansen EC, Volchkov I, Cho EJ, Lo WY, Lee D. Angew. Chem. Int. Ed. 2010; 49: 4261
    PubMed
  • 116 Hayashi Y, Shoji M, Ishikawa H, Yamaguchi J, Tamaru T, Imai H, Nishigaya Y, Takabe K, Kakeya H, Osada H. Angew. Chem. Int. Ed. 2008; 47: 6657
    PubMed
  • 117 Evano G, Schaus JV, Panek JS. Org. Lett. 2004; 6: 525
    PubMed
  • 118 Del Valle DJ, Krische MJ. J. Am. Chem. Soc. 2013; 135: 10986
    PubMed
  • 119 Fujiwara K, Suzuki Y, Koseki N, Aki Y.-I, Kikuchi Y, Murata F, Yamamoto F, Kawamura M, Norikura T, Matsue H, Murai A, Katoono R, Kawai H, Suzuki T. Angew. Chem. Int. Ed. 2014; 53: 780
    PubMed
  • 120 Hara A, Morimoto R, Iwasaki Y, Saitoh T, Ishikawa Y, Nishiyama S. Angew. Chem. Int. Ed. 2012; 51: 9877
    PubMed
  • 121 Kobayashi J, Shimbo K, Sato M, Shiro M, Tsuda M. Org. Lett. 2000; 2: 2805
    PubMed
  • 122 Zuercher WJ, Hashimoto M, Grubbs RH. J. Am. Chem. Soc. 1996; 118: 6634
  • 123 Harrity JPA, Visser MS, Gleason JD, Hoveyda AH. J. Am. Chem. Soc. 1997; 119: 1488
  • 124 Stragies R, Blechert S. J. Am. Chem. Soc. 2000; 122: 9584
  • 125 Buschmann N, Rückert A, Blechert S. J. Org. Chem. 2002; 67: 4325
    PubMed
  • 126 Holub N, Neidhöfer J, Blechert S. Org. Lett. 2005; 7: 1227
    PubMed
  • 127 Böhrsch V, Neidhöfer J, Blechert S. Angew. Chem. Int. Ed. 2006; 45: 1302
    PubMed
  • 128 Böhrsch V, Blechert S. Chem. Commun. (Cambridge) 2006; 1968
    PubMed
  • 129 Stragies R, Blechert S. Synlett 1998; 169
  • 130 Wrobleski A, Sahasrabudhe K, Aubé J. J. Am. Chem. Soc. 2004; 126: 5475
    PubMed
  • 131 Henderson JA, Phillips AJ. Angew. Chem. Int. Ed. 2008; 47: 8499
    PubMed
  • 132 Pfeiffer MWB, Phillips AJ. J. Am. Chem. Soc. 2005; 127: 5334
    PubMed
  • 133 Miura Y, Hayashi N, Yokoshima S, Fukuyama T. J. Am. Chem. Soc. 2012; 134: 11995
    PubMed
  • 134 Li J, Lee D. Chem. Sci. 2012; 3: 3296
  • 135 Takao K.-I, Nanamiya R, Fukushima Y, Namba A, Yoshida K, Tadano K.-I. Org. Lett. 2013; 15: 5582
    PubMed
  • 136 Han J.-C, Li F, Li C.-C. J. Am. Chem. Soc. 2014; 136: 13610
    PubMed
  • 137 Hansen EC, Lee D. Acc. Chem. Res. 2006; 39: 509
    PubMed
  • 138 Villar H, Frings M, Bolm C. Chem. Soc. Rev. 2007; 36: 55
    PubMed
  • 139 Ulman M, Grubbs RH. Organometallics 1998; 17: 2484
  • 140 Hoye TR, Donaldson SM, Vos TJ. Org. Lett. 1999; 1: 277
    PubMed
  • 141 Schramm MP, Reddy DS, Kozmin SA. Angew. Chem. Int. Ed. 2001; 40: 4274
    PubMed
  • 142 Lloyd-Jones GC, Margue RG, de Vries JG. Angew. Chem. Int. Ed. 2005; 44: 7442
    PubMed
  • 143 Sohn J.-H, Kim KH, Lee H.-Y, No ZS, Ihee H. J. Am. Chem. Soc. 2008; 130: 16506
    PubMed
  • 144 Kim KH, Ok T, Lee K, Lee H.-Y, Chang KT, Ihee H, Sohn J.-H. J. Am. Chem. Soc. 2010; 132: 12027
    PubMed
  • 145 Lee OS, Kim KH, Kim J, Kwon K, Ok T, Ihee H, Lee H.-Y, Sohn J.-H. J. Org. Chem. 2013; 78: 8242
    PubMed
  • 146 Lee Y.-J, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 10652
    PubMed
  • 147 Clavier H, Correa A, Escudero-Adán EC, Benet-Buchholz J, Cavallo L, Nolan SP. Chem.–Eur. J. 2009; 15: 10244
    PubMed
  • 148 Lippstreu JJ, Straub BF. J. Am. Chem. Soc. 2005; 127: 7444
    PubMed
  • 149 Nuñez-Zarur F, Solans-Monfort X, Rodríguez-Santiago L, Pleixats R, Sodupe M. Chem.–Eur. J. 2011; 17: 7506
    PubMed
  • 150 Zuercher WJ, Scholl M, Grubbs RH. J. Org. Chem. 1998; 63: 4291
  • 151 Huang J, Xiong H, Hsung RP, Rameshkumar C, Mulder JA, Grebe TP. Org. Lett. 2002; 4: 2417
    PubMed
  • 152 Choi T.-L, Grubbs RH. Chem. Commun. (Cambridge) 2001; 2648
  • 153 Timmer MSM, Ovaa H, Filippov DV, van der Marel GA, van Boom JH. Tetrahedron Lett. 2001; 42: 8231
  • 154 Wu C.-J, Madhushaw RJ, Liu R.-S. J. Org. Chem. 2003; 68: 7889
    PubMed
  • 155 Maifeld SV, Miller RL, Lee D. J. Am. Chem. Soc. 2004; 126: 12228
    PubMed
  • 156 Zhao Y, Hoveyda AH, Schrock RR. Org. Lett. 2011; 13: 784
    PubMed
  • 157 Betkekar VV, Panda S, Kaliappan KP. Org. Lett. 2012; 14: 198
    PubMed
  • 158 Miller RL, Maifeld SV, Lee D. Org. Lett. 2004; 6: 2773
    PubMed
  • 159 Matsuda T, Yamaguchi Y, Murakami M. Synlett 2008; 561
  • 160 Layton ME, Morales CA, Shair MD. J. Am. Chem. Soc. 2002; 124: 773
    PubMed
  • 161 Morales CA, Layton ME, Shair MD. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 12036
    PubMed
  • 162 Hansen EC, Lee D. J. Am. Chem. Soc. 2003; 125: 9582
    PubMed
  • 163 Hansen EC, Lee D. J. Am. Chem. Soc. 2004; 126: 15074
    PubMed
  • 164 Grimwood ME, Hansen HC. Tetrahedron 2009; 65: 8132
  • 165 Kim M, Miller RL, Lee D. J. Am. Chem. Soc. 2005; 127: 12818
    PubMed
  • 166 Yun SY, Kim M, Lee D, Wink DJ. J. Am. Chem. Soc. 2009; 131: 24
    PubMed
  • 167 Wang K.-P, Yun SY, Lee D. J. Am. Chem. Soc. 2009; 131: 15114
    PubMed
  • 168 van Otterlo W. AL, Ngidi EL, de Koning CB, Fernandes MA. Tetrahedron Lett. 2004; 45: 659
  • 169 Kinoshita A, Mori M. J. Org. Chem. 1996; 61: 8356
  • 170 Kinoshita A, Mori M. Heterocycles 1997; 46: 287
  • 171 Debleds O, Campagne J.-M. J. Am. Chem. Soc. 2008; 130: 1562
    PubMed
  • 172 Graham TJA, Gray EE, Burgess JM, Goess BC. J. Org. Chem. 2010; 75: 226
    PubMed
  • 173 Aggarwal VK, Astle CJ, Rogers-Evans M. Org. Lett. 2004; 6: 1469
    PubMed
  • 174 Brenneman JB, Martin SF. Org. Lett. 2004; 6: 1329
    PubMed
  • 175 Mori M, Tomita T, Kita Y, Kitamura T. Tetrahedron Lett. 2004; 45: 4397
  • 176 Reddy DS, Kozmin SA. J. Org. Chem. 2004; 69: 4860
    PubMed
  • 177 Gao X, Woo SK, Krische MJ. J. Am. Chem. Soc. 2013; 135: 4223
    PubMed
  • 178 Li J, Lee D. Chem.–Asian J. 2010; 5: 1298
    PubMed
  • 179 Honda T, Namiki H, Kaneda K, Mizutani H. Org. Lett. 2004; 6: 87
    PubMed
  • 180 Boyer F.-D, Hanna I, Ricard L. Org. Lett. 2004; 6: 1817
    PubMed
  • 181 Schubert M, Metz P. Angew. Chem. Int. Ed. 2011; 50: 2954
    PubMed
  • 182 Mukherjee S, Lee D. Org. Lett. 2009; 11: 2916
    PubMed
  • 183 Dineen TA, Roush WR. Org. Lett. 2004; 6: 2043
    PubMed
  • 184 Movassaghi M, Piizzi G, Siegel DS, Piersanti G. Angew. Chem. Int. Ed. 2006; 45: 5859
    PubMed
  • 185 Poulin J, Grise-Bard CM, Barriault L. Angew. Chem. Int. Ed. 2012; 51: 2111
    PubMed
  • 186 Betkekar VV, Sayyad AA, Kaliappan KP. Org. Lett. 2014; 16: 5540
    PubMed
  • 187 Molawi K, Delpont N, Echavarren AM. Angew. Chem. Int. Ed. 2010; 49: 3517
    PubMed
  • 188 Lee J, Parker KA. Org. Lett. 2012; 14: 2682
    PubMed
  • 189 Wei H, Qiao C, Liu G, Yang Z, Li C.-C. Angew. Chem. Int. Ed. 2013; 52: 620
    PubMed
  • 190 Kitamura T, Mori M. Org. Lett. 2001; 3: 1161
    PubMed
  • 191 Rückert A, Eisele D, Blechert S. Tetrahedron Lett. 2001; 42: 5245
  • 192 Mori M, Wakamatsu H, Tonogaki K, Fujita R, Kitamura T, Sato Y. J. Org. Chem. 2005; 70: 1066
    PubMed
  • 193 Zhu Z.-B, Shi M. Org. Lett. 2010; 12: 4462
    PubMed
  • 194 Kress S, Weckesser J, Schulz SR, Blechert S. Eur. J. Org. Chem. 2013; 1346
  • 195 Basso A, Banfi L, Riva R, Guanti G. Tetrahedron 2006; 62: 8830
  • 196 Groaz E, Banti D, North M. Tetrahedron Lett. 2007; 48: 1927
  • 197 Spandl RJ, Rudyk H, Spring DR. Chem. Commun. (Cambridge) 2008; 3001
    PubMed
  • 198 Kim M, Lee D. J. Am. Chem. Soc. 2005; 127: 18024
    PubMed
  • 199 Li J, Park S, Miller RL, Lee D. Org. Lett. 2009; 11: 571
    PubMed
  • 200 Wengrovius JH, Sancho J, Schrock RR. J. Am. Chem. Soc. 1981; 103: 3932
  • 201 Schrock RR. Polyhedron 1995; 14: 3177
  • 202 Fürstner A, Davies PW. Chem. Commun. (Cambridge) 2005; 2307
    PubMed
  • 203 Hérisson J.-L, Chauvin Y. Makromol. Chem. 1971; 141: 161
  • 204 Katz TJ, McGinnis J. J. Am. Chem. Soc. 1975; 97: 1592
  • 205 McCullough LG, Listemann ML, Schrock RR, Churchill MR, Ziller JW. J. Am. Chem. Soc. 1983; 105: 6729
  • 206 Zhu J, Jiu G, Lin Z. Organometallics 2006; 25: 1812
  • 207 Krouse SA, Schrock RR. Macromolecules 1989; 22: 2569
  • 208 Aguilera B, Wolf LB, Nieczypor P, Rutjes FPJT, Overkleeft HS, van Hest JCM, Schoemaker HE, Wang B, Mol JC, Fürstner A, Overhand M, van der Marel GA, van Boom JH. J. Org. Chem. 2001; 66: 3584
    PubMed
  • 209 Jsselstijn MI, Kaiser J, van Delft FL, Schoemaker HE, Rutjes FPJT. Amino Acids 2003; 24: 263
    PubMed
  • 210 IJsselstijn M, Aguilera B, van der Marel GA, van Boom JH, van Delft FL, Schoemaker HE, Overkleeft HS, Rutjes FPJT, Overhand M. Tetrahedron Lett. 2004; 45: 4379
  • 211 Ghalit N, Poot AJ, Fürstner A, Rijkers DTS, Liskamp RM. Org. Lett. 2005; 7: 2961
    PubMed
  • 212 Doyle D, Murphy PV. Carbohydr. Res. 2008; 343: 2535
    PubMed
  • 213 Bauer EB, Szafert S, Hampel F, Gladysz JA. Organometallics 2003; 22: 2184
  • 214 Bauer EB, Hampel F, Gladysz JA. Adv. Synth. Catal. 2004; 346: 812
  • 215 Lysenko S, Volbeda J, Jones PG, Tamm M. Angew. Chem. Int. Ed. 2012; 51: 6757
    PubMed
  • 216 Fürstner A, Seidel G. J. Organomet. Chem. 2000; 606: 75
  • 217 Fürstner A, Rumbo A. J. Org. Chem. 2000; 65: 2608
    PubMed
  • 218 Fürstner A, Grela K. Angew. Chem. Int. Ed. 2000; 39: 1234
    PubMed
  • 219 Fürstner A, Mathes C, Grela K. Chem. Commun. (Cambridge) 2001; 1057
  • 220 Vintonyak VV, Maier M. Angew. Chem. Int. Ed. 2007; 46: 5209
    PubMed
  • 221 Vintonyak VV, Calà M, Lay F, Kunze B, Sasse F, Maier M. Chem.–Eur. J. 2008; 14: 3709
    PubMed
  • 222 Fürstner A, Bindl M, Jean L. Angew. Chem. Int. Ed. 2007; 46: 9275
    PubMed
  • 223 Fouché M, Rooney L, Barrett AGM. J. Org. Chem. 2012; 77: 3060
    PubMed
  • 224 Hickmann V, Alcarazo M, Fürstner A. J. Am. Chem. Soc. 2010; 132: 11042
    PubMed
  • 225 Fürstner A, Larionov O, Flügge S. Angew. Chem. Int. Ed. 2007; 46: 5545
    PubMed
  • 226 Freudenberger JH, Schrock RR, Churchill MR, Rheingold AL, Ziller JW. Organometallics 1984; 3: 1563
  • 227 Bindl M, Stade R, Heilmann EK, Picot A, Goddard R, Fürstner A. J. Am. Chem. Soc. 2009; 131: 9468
    PubMed
  • 228 Kyle AF, Jakubec P, Cockfield DM, Cleator E, Skidmore J, Dixon DJ. Chem. Commun. (Cambridge) 2011; 47: 10037
    PubMed
  • 229 Fürstner A, Radkowski K. Chem. Commun. (Cambridge) 2002; 2182
    PubMed
  • 230 Lacombe F, Radkowski K, Seidel G, Fürstner A. Tetrahedron 2004; 60: 7315
  • 231 Heppekausen J, Stade R, Goddard R, Fürstner A. J. Am. Chem. Soc. 2010; 132: 11045
    PubMed
  • 232 Sundararaju B, Fürstner A. Angew. Chem. Int. Ed. 2013; 52: 14050
    PubMed
  • 233 Radkowski K, Sundararaju B, Fürstner A. Angew. Chem. Int. Ed. 2013; 52: 355
    PubMed
  • 234 Lehr K, Mariz R, Leseurre L, Gabor B, Fürstner A. Angew. Chem. Int. Ed. 2011; 50: 11373
    PubMed
  • 235 Micoine K, Persich P, Llaveria J, Lam M.-H, Maderna A, Loganzo F, Fürstner A. Chem.–Eur. J. 2013; 19: 7370
    PubMed
  • 236 Willwacher J, Fürstner A. Angew. Chem. Int. Ed. 2014; 53: 4217
    PubMed
  • 237 Neuhaus CM, Liniger M, Stieger M, Altmann K.-H. Angew. Chem. Int. Ed. 2013; 52: 5866
    PubMed
  • 238 Willwacher J, Kausch-Busies N, Fürstner A. Angew. Chem. Int. Ed. 2012; 51: 12041
    PubMed
  • 239 Ungeheuer F, Fürstner A. Chem.–Eur. J. 2015; 21: 11387
    PubMed
  • 240 Zhang W, Moore JS. J. Am. Chem. Soc. 2005; 127: 11863
    PubMed
  • 241 Zhang W, Moore JS. Angew. Chem. Int. Ed. 2006; 45: 4416
    PubMed
  • 242 Ge P.-H, Fu W, Herrmann WA, Herdtweck E, Campana C, Adams RD, Bunz UHF. Angew. Chem. Int. Ed. 2000; 39: 3607
    PubMed
  • 243 Zhang W, Moore JS. J. Am. Chem. Soc. 2004; 126: 12796
    PubMed