Recent Progress in the Synthetic Assembly of 2-Cyclopentenones

Abstract

An overview of the most important synthetic strategies currently available for the preparation of cyclopent-2-enones is presented and illustrated with recent applications.

1 Introduction

2 Multicomponent Ring Assembly

3 Cyclizations

4 Transformations of Existing Cyclic Systems

5 Miscellaneous Methods

6 Conclusions

Key words

cyclopentenones - cyclization - carbocycles - ring closure - rearrangement - annulation

• References

• 1a Gibson SE, Lewis SE, Mainolfi N. J. Organomet. Chem. 2004; 689: 3873
• 1b Roche SP, Aitken DJ. Eur. J. Org. Chem. 2010; 5339
• 1c Mehta G, Srikrishna A. Chem. Rev. 1997; 97: 671
• 1d Hudlicky T, Price JD. Chem. Rev. 1989; 89: 1467
• 1e Trost BM. Chem. Soc. Rev. 1982; 11: 141
• 1f Marsden SP. Science of Synthesis . Vol. 26. Cossy J. Thieme; Stuttgart: 2004: 1045
• 2 Ellison RA. Synthesis 1973; 397
• 3 Coote SC, O'Brien P, Whitwood AC. Org. Biomol. Chem. 2008; 6: 4299
• 4 Basavaiah D, Reddy BS, Badsara SS. Chem. Rev. 2010; 110: 5447
• 5 Declerck V, Martinez J, Lamaty F. Chem. Rev. 2009; 109: 1
• 6 Koech PK, Krische MJ. J. Am. Chem. Soc. 2004; 126: 5350
• 7 Krafft ME, Cran JW. Synlett 2005; 1263
• 8a Smith III AB, Branca SJ, Guaciaro MA, Wovkulich PM, Korn A. Org. Synth. 1983; 61: 65
• 8b Kim KM, Chung KH, Kim JN, Ryu EK. Synthesis 1993; 283
• 8c Adam W, Saha-Moeller CR, Zhao C.-G. Org. React. 2002; 61: 219
• 9a Negishi E.-i. Tetrahedron 2000; 56: 10197
• 9b Miller MW, Johnson CR. J. Org. Chem. 1997; 62: 1582
• 9c Dyker G, Markwitz H, Henkel G. Eur. J. Org. Chem. 2001; 2415
• 9d Molander GA, Ham J, Seapy DG. Tetrahedron 2007; 63: 768
• 10 Liu K.-M, Chau C.-M, Sha C.-K. Chem. Commun. 2008; 91
• 11 Cho DJ, Wu CJ ;, S, S.; Han W.-S, Kang SO, Lee BY. Organometallics 2006; 25: 2133
• 12a Morisaki Y, Imoto H, Hirano K, Hayashi T, Chujo Y. J. Org. Chem. 2011; 76: 1795
• 12b Thaler T, Guo L.-N, Steib AK, Raducan M, Karaghiosoff K, Mayer P, Knochel P. Org. Lett. 2011; 13: 3182
• 12c Wei C.-H, Mannathan S, Cheng C.-H. J. Am. Chem. Soc. 2011; 133: 6942
• 12d Piovesana S, Scarpino Schietroma DM, Tulli LG, Monaco MR, Bella M. Chem. Commun. 2010; 46: 5160
• 12e Sibi MP, Manyem S. Tetrahedron 2000; 56: 8033
• 13a Perdicchia D, Jørgensen KA. J. Org. Chem. 2007; 72: 3565
• 13b Yang L, Xu L.-W, Zhou W, Li L, Xia C.-G. Tetrahedron Lett. 2006; 47: 7723
• 13c Rana NK, Selvakumar S, Singh VK. J. Org. Chem. 2010; 75: 2029
• 14a Krishna TR, Jayaraman N. Tetrahedron 2004; 60: 10325
• 14b Li J.-H, Wang D.-P, Xie Y.-X. Tetrahedron Lett. 2005; 46: 4941
• 15 Guo H.-C, Ma J.-A. Angew. Chem. Int. Ed. 2006; 45: 354
• 16 Gerdil R, Liu H, Bernardinelli G. Helv. Chim. Acta 1999; 82: 418
• 17a Kelly JM, Leeper FJ. Tetrahedron Lett. 2012; 53: 819
• 17b Tolstikov GA, Miftakhov MS, Danilova NA, Vel’der YaL, Spirikhin LV. Synthesis 1989; 625
• 18a Demir AS, Enders D. Tetrahedron Lett. 1989; 30: 1705
• 18b Mukaiyama T, Ohsumi T. Chem. Lett. 1983; 875
• 18c Lakhvich FA, Lis LG, Pap AA, Rubinov DB, Zheldakova TA, Akhrem AA. Zh. Org. Khim. 1988; 24: 518
• 19a Schulé A, Liang H, Vors J.-P, Ciufolini MA. J. Org. Chem. 2009; 74: 1588
• 19b Altenbach RJ, Brune ME, Buckner SA, Coghlan MJ, Daza AV, Fabiyi A, Gopalakrishnan M, Henry RF, Khilevich A, Kort ME, Milicic I, Scott VE, Smith JC, Whiteaker KL, Carroll WA. J. Med. Chem. 2006; 49: 6869
• 20a Kobayashi Y, Murugesh MG, Nakano M, Takahisa E, Usmani SB, Ainai T. J. Org. Chem. 2002; 67: 7110
• 20b Weaving R, Roulland E, Monneret C, Florent J.-C. Tetrahedron Lett. 2003; 44: 2579
• 20c Shi M, Zhang W. Tetrahedron 2005; 61: 11887
• 21a Mizuno M, Inoue H, Naito T, Zhou L, Nishiyama H. Chem. Eur. J. 2009; 15: 8985
• 21b Das J, Le Cavelier F, Rouden J, Blanchet J. Eur. J. Org. Chem. 2011; 6628
• 22a Pete J.-P In CRC Handbook of Organic Photochemistry and Photobiology . 2nd ed.; Horspool W, Lenci F. CRC Press; Boca Raton: 2003. Chap. 71, 1-14
• 22b Le Liepvre M, Ollivier J, Aitken DJ. Eur. J. Org. Chem. 2009; 5953
• 22c Margaretha P In Synthetic Organic Photochemistry . Griesbeck AG, Mattay J. Marcel Dekker; New York: 2005. Chap. 8, 211-237
• 23a Xu H, Wolf C. Angew. Chem. Int. Ed. 2011; 50: 12249
• 23b Canales E, Corey EJ. Org. Lett. 2008; 10: 3271
• 23c Northrup AB, MacMillan DW. C. J. Am. Chem. Soc. 2002; 124: 2458
• 24a Henry SS, Brady MD, Laird DL. T, Ruble JC, Varie DL, Monn JA. Org. Lett. 2012; 14: 2662
• 24b Garcia Ruano JL, Alonso M, Cruz D, Fraile A, Martin MR, Peromingo MT, Tito A, Yuste F. Tetrahedron 2008; 64: 10546
• 25 Menjo Y, Hamajima A, Sasaki N, Hamada Y. Org. Lett. 2011; 13: 5744
• 26 Lee A, Reisinger CM, List B. Adv. Synth. Catal. 2012; 354: 1701
• 27a Schore NE. Org. React. 1991; 40: 1
• 27b Geis O, Schmalz H.-G. Synthesis 1998; 911
• 27c Brummond KM, Kent JL. Tetrahedron 2000; 56: 3263
• 27d Laschat S, Becheanu A, Bell T, Baro A. Synlett 2005; 2547
• 27e Lee H.-W, Kwong F.-Y. Eur. J. Org. Chem. 2010; 789
• 27f Blanco-Urgoiti J, Añorbe L, Pérez-Serrano L, Domínguez G, Pérez-Castells J. Chem. Soc. Rev. 2004; 33: 32
• 28 Gibson SE, Mainolfi N. Angew. Chem. Int. Ed. 2005; 44: 3022
• 29 Shibata T. Adv. Synth. Catal. 2006; 348: 2328
• 30 The Pauson-Khand Reaction: Scope Variations and Applications. Torres RR. Wiley; Chichester: 2012
• 31 For leading references, see: Wu N, Deng L, Liu L, Liu Q, Li C, Yang Z. Chem. Asian J. 2013; 8: 65
• 32 Morimoto T, Kakiuchi K. Angew. Chem. Int. Ed. 2004; 43: 5580
• 33 Hong BC, Dange NS, Yen P.-J, Lee G.-H, Liao J.-H. Org. Lett. 2012; 14: 5346
• 34 Su S, Rodriguez EA, Baran PS. J. Am. Chem. Soc. 2011; 133: 13922
• 35 Tap A, Jouanneau M, Galvani G, Sorin G, Lannou M.-I, Ferezou J.-P, Ardisson J. Org. Biomol. Chem. 2012; 10: 8140
• 36 Turlington M, Du Y, Oqtrum SG, Santosh V, Wren K, Lin T, Sabat M, Pu L. J. Am. Chem. Soc. 2011; 133: 11780
• 37 Morisaki Y, Kondo T, Mitsudo T.-A. Org. Lett. 2000; 2: 949
• 38 Huang Q, Hua R. Chem. Eur. J. 2009; 13: 3817
• 39 Ohashi M, Taniguchi T, Ogoshi S. J. Am. Chem. Soc. 2011; 133: 14900
• 40 Barluenga J, Barrio P, Riesgo L, López LA, Tomás M. J. Am. Chem. Soc. 2007; 129: 14422
• 41 Barluenga J, Álvarez-Fernández A, Suárez-Sobrino ÁL, Tomás M. Angew. Chem. Int. Ed. 2012; 51: 183
• 42 Qi X, Ready JM. Angew. Chem. Int. Ed. 2008; 47: 7068
• 43 Miller JA, Pugh AW, Ullah GM, Welsh GM. Tetrahedron Lett. 2001; 42: 955
• 44 Tius MA. Acc. Chem. Res. 2003; 36: 284
• 45 Hu H, Smith D, Cramer RE, Tius MA. J. Am. Chem. Soc. 1999; 121: 9895
• 46 Schultz-Fademrecht C, Tius MA, Grimme S, Wibbeling B, Hoppe D. Angew. Chem. Int. Ed. 2002; 41: 1532
• 47 Jacobsen CB, Jensen KL, Udmark J, Jørgensen KA. Org. Lett. 2011; 13: 4790
• 48 Feist H, Langer P. Synthesis 2008; 3877
• 49 Langer P, Kracke B. Synlett 2001; 1790
• 50 Shinohara Y, Kurata T, Kitano H, Matsumoto K, Takahashi I, Hosoi S, Ota T, Hatanaka M. Synlett 2002; 1245
• 51a Cai X.-h, Xie B. Res. J. Chem. Sci. 2011; 1: 120
• 51b Marjani K, Mohsen M, Arazi A, Ashouri A, Bourghani S, Rajabi M. Monatsh. Chem. 2009; 140: 1331
• 51c Marjani K, Mousavi M, Ashouri A, Arazi O, Bourghani S, Asgari M. J. Chem. Res. 2008; 398
• 51d Majani K, Asgari M, Ashouri A, Mahdavinia GH, Ahangar HA. Chin. Chem. Lett. 2009; 20: 401
• 52 Holtz E, Köhler V, Appel B, Langer P. Eur. J. Org. Chem. 2005; 532
• 53 Jose A, Lakshmi KC. S, Suresh E, Nair V. Org. Lett. 2013; 15: 1858
• 54 Gagnier SV, Larock RC. J. Am. Chem. Soc. 2003; 125: 4804
• 55 Li H, Liu L, Zhao F, Wang C, Wang C, Song Q, Zhang W.-X, Xi Z. J. Org. Chem. 2012; 77: 4793
• 56 Laroche C, Bertus P, Szymoniak J. Chem. Commun. 2005; 3030
• 57 Rigby JH, Wang Z. Org. Lett. 2003; 5: 263
• 58 Davie CP, Danheiser RL. Angew. Chem. Int. Ed. 2005; 44: 5867
• 59 Moser WH, Feltes LA, Sun L, Giese M, Farrell RW. J. Org. Chem. 2006; 71: 6542
• 60 Giese M, Moser WH. Org. Lett. 2008; 10: 4215
• 61 Li Z, Moser WH, Deng R, Sun L. J. Org. Chem. 2007; 72: 10254
• 62 Kurahashi T, Wu Y.-T, Meindl K, Rühl S, de Meijere A. Synlett 2005; 805
• 63 Kurteva VB, Afonso CA. M. Chem. Rev. 2009; 109: 6809
• 64 Nazarov IN, Zaretskaya II. Izv. Akad. Nauk. SSSR, Ser. Khim. 1944; 65
• 65a Rueping M, Ieawsuwan W, Antonchick AP, Nachtsheim BJ. Angew. Chem. Int. Ed. 2007; 46: 2097
• 65b Basak AK, Shimada N, Bow WF, Vicic DA, Tius MA. J. Am. Chem. Soc. 2010; 132: 8266
• 65c Bow WE, Basak AK, Jolit A, Vicic DA, Tius MA. Org. Lett. 2010; 12: 440
• 65d Rueping M, Ieawsuwan W. Chem. Commun. 2010; 11450
• 66a Bee C, Leclerc E, Tius MA. Org. Lett. 2003; 5: 4927
• 66b Aggarwal VK, Belfield AJ. Org. Lett. 2003; 5: 5075
• 66c Liang G, Trauner D. J. Am. Chem. Soc. 2004; 126: 9544
• 66d Janka M, He W, Haedicke IE, Fronczek FR, Frontier AJ, Eisenberg R. J. Am. Chem. Soc. 2006; 128: 5312
• 66e Cao P, Deng C, Zhou Y.-Y, Sun X.-L, Zheng J.-C, Xie Z, Tang Y. Angew. Chem. Int. Ed. 2010; 49: 4463
• 67a Pellissier H. Tetrahedron 2005; 61: 6479
• 67b Frontier AJ, Collinson C. Tetrahedron 2005; 61: 7577
• 67c Tius MA. Eur. J. Org. Chem. 2005; 2193
• 67d Habermas KL, Denmark SE. Org. React. 1994; 45: 1
• 67e Denmark SE In Comprehensive Organic Synthesis . Vol. 5. Paquette LA. Pergamon; Oxford: 1991: 751-784
• 67f Santelli-Rouvier C, Santelli M. Synthesis 1983; 429
• 68 Vaida T, Eisenberg R, Frontier AJ. ChemCatChem 2011; 3: 1531
• 69 Shimada N, Stewart C, Tius MA. Tetrahedron 2011; 67: 5851
• 70 Spencer III WT, Vaidya T, Frontier AJ. Eur. J. Org. Chem. 2013; 3621
• 71 Grant TN, Rieder CJ, West FG. Chem. Commun. 2009; 5676
• 72 Yaji K, Shindo M. Tetrahedron 2010; 66: 9808
• 73 Williams DR, Robinson LA, Nevill CR, Reddy JP. Angew. Chem. Int. Ed. 2007; 46: 915
• 74 Magnus P, Freund WA, Moorhead EJ, Rainey T. J. Am. Chem. Soc. 2012; 134: 6140
• 75 Kerr DJ, Flynn BL. Org. Lett. 2012; 14: 1740
• 76 Lebœuf D, Wright CM, Frontier AJ. Chem. Eur. J. 2013; 19: 4835
• 77 Kerr DJ, Miletic M, Chaplin JH, White JM, Flynn BL. Org. Lett. 2012; 14: 1732
• 78 Flynn BL, Manchala N, Krenske EH. J. Am. Chem. Soc. 2013; 135: 9156
• 79 Cao P, Sun X.-L, Zhu B.-H, Shen Q, Xie Z, Tang Y. Org. Lett. 2009; 11: 3048
• 80 Li W.-DZ, Duo W.-G, Zhuang C.-H. Org. Lett. 2011; 13: 3538
• 81 Spencer III WT, Levin MD, Frontier AJ. Org. Lett. 2011; 13: 414
• 82 Rautenstrauch V. J. Org. Chem. 1984; 49: 950
• 83 Nakagawa D, Miyashita M, Tanino K. Tetrahedron Lett. 2010; 51: 2771
• 84 Shi X, Gorin DJ, Toste FD. J. Am. Chem. Soc. 2005; 127: 5802
• 85 Kato K, Kobayashi T, Fujimami T, Motodate S, Kusakabe T, Mochida T, Akita H. Synlett 2008; 1081
• 86 Zhang L, Wang S. J. Am. Chem. Soc. 2006; 128: 1442
• 87 An SE, Jeong J, Baskar B, Lee J, Seo J, Rhee YH. Chem. Eur. J. 2009; 15: 11837
• 88 Oh CH, Karmakar S. J. Org. Chem. 2009; 74: 370
• 89 Tang J.-M, Liu T.-A, Liu R.-S. J. Org. Chem. 2008; 73: 8479
• 90a Prunet J. Eur. J. Org. Chem. 2011; 3634
• 90b Metathesis in Natural Product Synthesis . Cossy J, Arseniyadis S, Meyer C. Wiley-VCH; Weinheim: 2010
• 90c Monfette S, Fogg DE. Chem. Rev. 2009; 109: 3783
• 90d Majumdar KC, Muhuri S, Islam R, Chattopadhyay B. Heterocycles 2009; 78: 1109
• 90e Chattopadhyay SK, Karmakar S, Biswas T, Majumdar KC, Rahaman H, Roy B. Tetrahedron 2007; 63: 3919
• 90f Villar H, Frings M, Bolm C. Chem. Soc. Rev. 2007; 36: 55
• 90g Brown RC. D, Satcharoen V. Heterocycles 2006; 70: 705
• 90h Schmidt B, Hermanns J. Curr. Org. Chem. 2006; 10: 1363
• 90i Deiters A, Martin SF. Chem. Rev. 2004; 104: 2199
• 90j Han SY, Chang S In Handbook of Metathesis . Vol. 2. Grubbs RH. Wiley-VCH; Weinheim: 2010. Chap. 2, 5-127
• 91 Funel J.-A, Prunet J. J. Org. Chem. 2004; 69: 4555
• 92 Dübon P, Schelwies M, Helmchen G. Chem. Eur. J. 2008; 14: 6722
• 93 Miller AK, Hughes CC, Kennedy-Smith JJ, Gradl SN, Trauner D. J. Am. Chem. Soc. 2006; 128: 17057
• 94a Davis FA, Wu Y. Org. Lett. 2004; 6: 1269
• 94b Bullock K, Chong P, Davies R, Elitzin V, Hatcher M, Jackson M, Liu B, Patterson D, Powers J, Salmons M, Tabet E, Toczko M. Top. Catal. 2012; 55: 446
• 95 Harmata M, Wacharasindhu S. Org. Lett. 2005; 7: 2563
• 96 Pfeiffer MW. B, Phillips AJ. J. Am. Chem. Soc. 2005; 127: 5334
• 97 Toueg J, Prunet J. Synlett 2006; 2807
• 98 Diver ST, Guissert AJ. Chem. Rev. 2004; 104: 1317
• 99 Ray D, Paul S, Brahma S, Ray JK. Tetrahedron Lett. 2007; 48: 8005
• 100 Ray D, Ray JK. Org. Lett. 2007; 9: 191
• 101 Ray D, Mal SK, Ray JK. Synlett 2005; 2135
• 102 Morita A, Kuwahara S. Org. Lett. 2006; 8: 1613
• 103 Tanaka K, Fu GC. J. Am. Chem. Soc. 2001; 123: 11492
• 104a Tanaka K, Fu GC. J. Am. Chem. Soc. 2001; 124: 10296
• 104b Tanaka K, Fu GC. J. Am. Chem. Soc. 2003; 125: 9078
• 105 Miller AK, Banghart MR, Beaudry CM, Suh JM, Trauner D. Tetrahedron 2003; 59: 8919
• 106 Kuroda C, Honda S, Nagura Y, Koshio H, Shibue T, Takeshita T. Tetrahedron 2004; 60: 319
• 107 Lo C.-Y, Lin C.-C, Cheng H.-M, Liu R.-S. Org. Lett. 2006; 8: 3135
• 108 Srikrishna A, Kumar PP. Tetrahedron 2000; 56: 8189
• 109 Pearson AJ, Kim EH, Sun H. Tetrahedron 2010; 66: 4943
• 110 Mehta G, Shinde HM. Tetrahedron Lett. 2007; 48: 8297
• 111 Andrei M, Undheim K. Tetrahedron: Asymmetry 2004; 15: 53
• 112 Samanta S, Yasmin N, Kundu D, Ray JK. Tetrahedron Lett. 2010; 51: 4132
• 113 Kitamura M, Chiba S, Narasaka K. Chem. Lett. 2004; 33: 942
• 114 Al-Tel TH, Semreen MH, Voelter W. Org. Biomol. Chem. 2010; 8: 5375
• 115 Christoffers J, Werner T, Frey W, Baro A. Chem. Eur. J. 2004; 10: 1042
• 116 Li W.-DZ, Wang Y.-Q. Org. Lett. 2003; 5: 2931
• 117 Cho YS, Carcache DA, Tian Y, Li Y.-M, Danishefsky SJ. J. Am. Chem. Soc. 2004; 126: 14358
• 118 Yan B, Spilling CD. J. Org. Chem. 2008; 73: 5385
• 119 Xu Y, McLaughlin M, Chen C.-y, Reamer RA, Dormer PG, Davies IW. J. Org. Chem. 2009; 74: 5100
• 120 Deng G, Xu B, Wang J. Tetrahedron 2005; 61: 10811
• 121 Zhuo X, Xiang K, Zhang F.-M, Tu Y.-Q. J. Org. Chem. 2011; 76: 6918
• 122 Piancatelli G, D’Auria M, D’Onofrio F. Synthesis 1994; 867
• 123 Faza ON, López CS, Álvarez R, de Lera ÁR. Chem. Eur. J. 2004; 10: 4324
• 124a Csákÿ AG, Contreras C, Mba M, Plumet J. Synlett 2002; 1451
• 124b Csákÿ AG, Mba M, Plumet J. Synlett 2003; 2092
• 125 Harikrishna M, Mohan HR, Dubey PK, Subbaraju GV. Synth. Commun. 2009; 39: 2763
• 126 Ulbrich K, Kreitmeier P, Reiser O. Synlett 2010; 2037
• 127 Yin B.-L, Wu Y.-L, Lai J.-Q. Eur. J. Org. Chem. 2009; 2695
• 128 Veits GK, Wenz DR, Read de Alaniz J. Angew. Chem. Int. Ed. 2010; 49: 9484
• 129 Reddy BV. S, Narasimhulu G, Lakshumma PS, Reddy YV, Yadav JS. Tetrahedron Lett. 2012; 53: 1776
• 130 Li S.-W, Batey RA. Chem. Commun. 2007; 3759
• 131 Wenz DR, Read de Alaniz J. Org. Lett. 2013; 15: 3250
• 132 Jung ME, Yoo D. J. Org. Chem. 2007; 72: 8565
• 133a Nunes JP. M, Veiros LF, Vaz PD, Afonso CA. M, Caddick S. Tetrahedron 2011; 67: 2779
• 133b Caddick S, Cheung S, Doyle VE, Frost LM, Soscia MG, Delisser VM, Williams MR. V, Etheridge ZE. Khan S, Hitchcock PB, Pairaudeau G, Vile S. Tetrahedron 2001; 57: 6295
• 134a Zou W, Shao H, Wu S.-H. Carbohydr. Res. 2004; 339: 2475
• 134b Zou W, Wang Z, Lacroix E, Wu S.-H, Jennings HJ. Carbohydr. Res. 2001; 334: 223
• 135 Shipe W, Sorensen EJ. J. Am. Chem. Soc. 2006; 128: 7025
• 136 Matoušová E, Růžička A, Kuneš J, Králová J, Pour M. Chem. Commun. 2011; 47: 9390
• 137 Li F, Ding C, Wang M, Yao Q, Zhang A. J. Org. Chem. 2011; 76: 2820
• 138 Pryde DC, Middleton DS, Stephenson PT, Wainwright P, Maddaford A, Zhang X, Leese D, Glen R, Hart J, Forrest N, Guyot T. Tetrahedron Lett. 2011; 52: 6415
• 139 Kumar BS, Mishra GP, Rao BV. Tetrahedron Lett. 2013; 54: 2845
• 140 Petrignet J, Prathap I, Chandrasekhar S, Yadav JS, Grée R. Angew. Chem. Int. Ed. 2007; 46: 6297
• 141 Hong F.-T, Lee K.-S, Liao C.-C. J. Chin. Chem. Soc. 2000; 47: 77
• 142 Kao T.-C, Chuang GJ, Liao C.-C. Angew. Chem. Int. Ed. 2008; 47: 7325
• 143a Leemans E, D’hooghe M, De Kimpe N. Chem. Rev. 2011; 111: 3268
• 143b Mack DJ, Njardarson JT. ACS Catal. 2013; 3: 272
• 144 Brown B, Hegedus LS. J. Org. Chem. 2000; 65: 1865
• 145 Mahuteau-Betzer F, Ghosez L. Tetrahedron 2002; 58: 6991
• 146 Gao FY, Burnell DJ. J. Org. Chem. 2006; 71: 356
• 147 Coquerel Y, Greene AE, Deprés J.-P. Org. Lett. 2003; 5: 4453
• 148 Carret S, Deprés J.-P. Angew. Chem. Int. Ed. 2007; 46: 6870
• 149 Varea T, Alcalde A, de Castillo CL, de Arellano CR, Cossio FP, Asensio G. J. Org. Chem. 2012; 77: 6327
• 150a Geng F, Liu J, Paquette LA. Org. Lett. 2002; 4: 71
• 150b Paquette LA, Geng F. Org. Lett. 2002; 4: 4547
• 151 Grant TN, West FG. J. Am. Chem. Soc. 2006; 128: 9348
• 152 Trost BM, Xia J, Maulide N. J. Am. Chem. Soc. 2008; 130: 17258
• 153 Pujanauski BG, Prasad BA. B, Sarpong R. J. Am. Chem. Soc. 2006; 128: 6787
• 154 Jung ME, Davidov P. Org. Lett. 2001; 3: 3025
• 155 Matsuda T, Tsuboi T, Murakami M. J. Am. Chem. Soc. 2007; 129: 12596
• 156 Mehta G, Umarye JD. Org. Lett. 2002; 4: 1063
• 157 Iqbal M, Duffy P, Evans P, Cloughley G, Allan B, Lledó A, Verdaguer X, Riera A. Org. Biomol. Chem. 2008; 6: 4649
• 158 Demuynck AL.W, Levecque P, Kidane A, Gammon DW, Sickle E, Jacobs PA, De Vos DE, Sels BF. Adv. Synth. Catal. 2010; 352: 3419
• 159 Shindo M, Sato Y, Shishido K. J. Org. Chem. 2001; 66: 7818
• 160 Shindo M, Sato Y, Shishido K. Tetrahedron Lett. 2002; 43: 5039
• 161a Kuhn C, Skaltsounis L, Monneret C, Florent J.-C. Eur. J. Org. Chem. 2003; 2585
• 161b Kuhn C, Roulland E, Madelmont J.-C, Monneret C, Florent J.-C. Org. Biomol. Chem. 2004; 2: 2028
• 162 Ballini R, Boscia G, Fiorini D, Gil MV, Petrini M. Org. Lett. 2001; 3: 1265
• 163 Pal R, Clark RJ, Manoharan M, Alabugin IV. J. Org. Chem. 2010; 75: 8689
• 164 Heck M.-P, Matt C, Wagner A, Toupet L, Mioskowski C. Eur. J. Org. Chem. 2010; 966