Petasis反应研究进展

doi:10.6023/cjoc1202092

摘要/Abstract

Petasis反应是构建氨基酸、氨基醇及其相应的衍生物等结构片段的有效方法之一, 其中手性Petasis反应已应用于天然产物和药物的片段合成. 就文献中机理、组分、反应条件等方面的研究进行了综述, 并对 Petasis反应的应用实例进行了讨论.

关键词: Petasis反应, 有机硼化物, 多组分反应

Petasis reaction is a powerful method for the synthesis of α-amino acids, β-amino alcohols and their derivatives. Chiral Petasis reaction has been applied in synthesis of nature products and drugs. This review describes the mechanism, reaction components and reaction conditions of Petasis reaction, and the applications of Petasis reaction are also discussed in the paper.

Key words: Petasis reaction, organoboron compounds, multicomponent reactions

引用此文

于涛, 李慧, 伍新燕, 杨军. Petasis反应研究进展[J]. 有机化学, 2012, 32(10): 1836-1845.

Yu Tao, Li Hui, Wu Xinyan, Yang Jun. Progress in Petasis Reaction[J]. Chin. J. Org. Chem., 2012, 32(10): 1836-1845.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Zhu, J.; Bienaymé, H. Multicomponent Reactions, Wiley-VCH, Weineim, Germany, 2005, pp. 206～223.

[2] Portlock, D. E.; Ostaszewski, R.; Naskar, D.; West, L. Tetrahedron Lett. 2003, 44, 603.

[3] Kalinski, C.; Lemoine, H.; Schmidt, J.; Burdack, C. Synthesis 2008, 4007.

[4] Jiang, B.; Xu, M. Angew. Chem., Int. Ed. 2004, 43, 2543.

[5] McReynolds, M. D.; Hanson, P. R. Chemtracts 2001, 14, 796.

[6] Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34, 583.

[7] Hall, D. Boronic Acid: Preparation and Applications in Organic Synthesis and Medicine, Wiley-VCH, Weinheim, Germany, 2005, pp. 279～304.

[8] Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P. M. P. Chem. Rev. 2010, 110, 6169.

[9] Hansen, T. K.; Schlienger, N.; Bryce, M. R. Tetrahedron Lett. 1999, 40, 3651.

[10] Jiang, B.; Xu, M. Org. Lett. 2002, 4, 4077.

[11] Neogi, S.; Roy, A.; Naskar, D. J. Comb. Chem. 2010, 12, 75.

[12] Au, C. W. G.; Nash, R. J.; Pyne, S. G. Chem. Commun. 2010, 46, 713.

[13] Schlienger, N.; Bryce, M. R.; Hansen, T. K. Tetrahedron 2000, 56, 10023.

[14] Tao, J.; Li, S. Chin. J. Chem. 2010, 28, 41.

[15] Kaiser, P. F.; Churches, Q. I.; Hutton, C. A. Aust. J. Chem. 2007, 60, 799.

[16] Petasis, N. A. Aust. J. Chem. 2007, 60, 795.

[17] Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.

[18] Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445.

[19] Charville, H.; Jackson, D.; Hodges, G.; Whiting, A. Chem. Commun. 2010, 46, 1813.

[20] Al-Zoubi, R. M.; Marion, O.; Hall, D. G. Angew. Chem., Int. Ed. 2008, 47, 2876.

[21] Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 4196.

[22] Petasis, N. A.; Patel, Z. D. Tetrahedron Lett. 2000, 41, 9607.

[23] Machan, T.; Davis, A. S.; Liawruangrath, B.; Pyne, S. G. Tetrahedron 2008, 64, 2725.

[24] Petasis, N. A.; Goodman, A.; Zavialov, I. A. Tetrahedron 1997, 53, 16463.

[25] Berrée , F.; Debache, A.; Marsac, Y.; Carboni, B. Tetrahedron Lett. 2001, 42, 3591.

[26] Jiang, B.; Yang, C. G.; Gu, X. H. Tetrahedron Lett. 2001, 42, 2545.

[27] Voisin, A. S.; Bouillon, A.; Lancelot, J.-C.; Lesnard, A.; Oulyadi, H.; Rault, S. Tetrahedron Lett. 2006, 47, 2165.

[28] Kolomeitsev, A. A.; Kadyrov, A. A.; Szczepkowska-Sztolcman, J.; Milewska, M.; Koroniak, H.; Bissky, G.; Barten, J. A.; Roeschenthaler, G.-V. Tetrahedron Lett. 2003, 44, 8273.

[29] Koolmeister, T.; Sodergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5965.

[30] Koolmeister, T.; Sodergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969.

[31] Jourdan, H.; Gouhier, G.; Van Hijfte, L.; Angibaud, P.; Piettre, S. R. Tetrahedron Lett. 2005, 46, 8027.

[32] Stas, S.; Tehrani, K. A.; Laus, G. Tetrahedron 2008, 64, 3457.

[33] Morgan, I. R.; Yazici, A.; Pyne, S. G. Tetrahedron 2008, 64, 1409.

[34] Tremblay-Morin, J. P.; Raeppel, S.; Gaudette, F. Tetrahedron Lett. 2004, 45, 3471.

[35] Stas, S.; Tehrani, K. A. Tetrahedron 2007, 63, 8921.

[36] Konev, A. S.; Stas, S.; Novikov, M. S.; Khlebnikov, A. F.; Tehrani, K. A. Tetrahedron 2008, 64, 117.

[37] Tehrani, K. A.; Stas, S.; Lucas, B.; Kimpe, N. D. Tetrahedron 2009, 65, 1957.

[38] Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.

[39] Naskar, D.; Roy, A.; Seibel, W. L.; Portlock, D. E. Tetrahedron Lett. 2003, 44, 5819.

[40] Hong, Z.; Liu, L.; Sugiyama, M.; Fu, Y.; Wong, C.-H. J. Am. Chem. Soc. 2009, 131, 8352.

[41] Chang, Y. M.; Lee, S. H.; Nam, M. H.; Cho, M. Y.; Park, Y. S.; Yoon, C. M. Tetrahedron Lett. 2005, 46, 3053.

[42] Portlock, D. E.; Naskar, D.; West, L.; Li, M. Tetrahedron Lett. 2002, 43, 6845.

[43] Naskar, D.; Roy, A.; Seibel, W. L.; Portlock, D. E. Tetrahedron Lett. 2003, 44, 8865.

[44] Naskar, D.; Neogi, S.; Roy, A.; Mandal, A. B. Tetrahedron Lett. 2008, 49, 6762.

[45] Naskar, D.; Roy, A.; Seibel, W. L. Tetrahedron Lett. 2003, 44, 8861.

[46] Wang, Q.; Finn, M. G. Org. Lett. 2000, 2, 4063.

[47] Berree, F.; Debache, A.; Marsac, Y.; Collet, B.; Girard-Le Bleiz, P.; Carboni, B. Tetrahedron 2006, 62, 4027.

[48] Southwood, T. J.; Curry, M. C.; Hutton, C. A. Tetrahedron 2006, 62, 236.

[49] Churches, Q. I.; Stewart, H. E.; Cohen, S. B.; Shroder, A.; Turner, P.; Hutton, C. A. Pure Appl. Chem. 2008, 80, 687.

[50] Shevchuk, M. V.; Sorochinsky, A. E.; Khilya, V. P.; Romanenko, V. D.; Kukhar, V. P. Synlett 2010, 73.

[51] Golebiowski, A.; Klopfenstein, S. R.; Chen, J. J.; Shao, X. Tetrahedron Lett. 2000, 41, 4841.

[52] Font, D.; Heras, M.; Villalgordo, J. M. Tetrahedron 2008, 64, 5226.

[53] Prakash, G. K. S.; Mandal, M.; Schweizer, S.; Petasis, N. A.; Olah, G. A. Org. Lett. 2000, 2, 3173.

[54] Prakash, G. K. S.; Mandal, M.; Schweizer, S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2002, 67, 3718.

[55] Petasis, N. A.; Boral, S. Tetrahedron Lett. 2001, 42, 539.

[56] Petasis, N. A.; Butkevich, A. N. J. Organomet. Chem. 2009, 694, 1747.

[57] Grigg, R.; Sridharan, V.; Thayaparan, A. Tetrahedron Lett. 2003, 44, 9017.

[58] Kabalka, G. W.; Venkataiah, B.; Dong, G. Tetrahedron Lett. 2004, 45, 729.

[59] Kumagai, N.; Muncipinto, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2006, 45, 3635.

[60] Lou, S.; Schaus, S. E. J. Am. Chem. Soc. 2008, 130, 6922.

[61] Nanda, K. K.; Wesley Trotter, B. Tetrahedron Lett. 2005, 46, 2025.

[62] Yadav, J. S.; Reddy, B. V. S.; Lakshmi, P. N. J. Mol. Catal. A: Chem. 2007, 274, 101.

[63] Candeias, N. R.; Veiros, L. F.; Afonso, C. A. M.; Gois, P. M. P. Eur. J. Org. Chem. 2009, 1859.

[64] Candeias, N. R.; Cal, P. M. S. D.; Andre, V.; Duarte, M. T.; Gois, P. M. P. Tetrahedron 2010, 66, 2736.

[65] Klopfenstein, S. R.; Chen, J. J.; Golebiowski, A.; Li, M.; Peng, S. X.; Shao, X. Tetrahedron Lett. 2000, 41, 4835.

[66] Danieli, E.; Trabocchi, A.; Menchi, G.; Guarna, A. Eur. J. Org. Chem. 2007, 1659.

[67] Mieczkowski, A.; Kozmiński, W.; Jurczak, J. Synthesis 2010, 221.

[68] Thompson, K. A.; Hall, D. G. Chem. Commun. 2000, 2379.

[69] Regnier, T.; Berree, F.; Lavastre, O.; Carboni, B. Green Chem. 2007, 125.

[70] McLean, N. J.; Tye, H.; Whittaker, M. Tetrahedron Lett. 2004, 45, 993.

[71] Follmann, M.; Graul, F.; Schaefer, T.; Kopec, S.; Hamley, P. Synlett 2005, 1009.

[72] Sugiyama, S.; Arai, S.; Kiriyama, M.; Ishii, K. Chem. Pharm. Bull. 2005, 53, 100.

[73] Sugiyama, S.; Arai, S.; Ishii, K. Tetrahedron: Asymmetry 2004, 15, 3149.

[74] Neogi, S.; Roy, A.; Naskar, D. J. Comb. Chem. 2010, 12, 617.

[75] Davis, A. S.; Pyne, S. G.; Skelton, B. W.; White, A. H. J. Org. Chem. 2004, 69, 3139.

[76] Ritthiwigrom, T.; Pyne, S. G. Org. Lett. 2008, 10, 2769.

[77] Ritthiwigrom, T.; Willis, A. C.; Pyne, S. G. J. Org. Chem. 2010, 75, 815.

[78] Hong, Z.; Liu, L.; Hsu, C. C.; Wong, C. H. Angew. Chem., Int. Ed. 2006, 45, 7417.

[79] Au, C. W. G.; Pyne, S. G. J. Org. Chem. 2006, 71, 7097.

[80] Naskar, D.; Roy, A.; Seibel, W. L.; West, L.; Portlock, D. E. Tetrahedron Lett. 2003, 44, 6297.

[81] Portlock, D. E.; Naskar, D.; West, L.; Ostaszewski, R.; Chen, J. J. Tetrahedron Lett. 2003, 44, 5121.