English
新闻公告
More
化学进展 2010, Vol. 22 Issue (07): 1341-1352 前一篇   后一篇

• 特约稿 •

过渡金属催化的1,n-烯炔类化合物的不对称环异构化反应

陈茂   翁玥   雷爱文*   

  1. (武汉大学化学与分子科学学院    武汉  430000)
  • 收稿日期:2010-02-25 出版日期:2010-07-24 发布日期:2010-07-02
  • 通讯作者: 雷爱文 E-mail:aiwenlei@whu.edu.cn

Asymmetric Cycloisomerization of 1,n-Enynes Catalyzed by Transition Metals

Chen Mao    Weng Yue    Lei Aiwen*   

  1. (College of Chemistry and Molecular Sciences, Wuhan University, Wuhan  430000, China)
  • Received:2010-02-25 Online:2010-07-24 Published:2010-07-02
  • Contact: Lei Aiwen E-mail:aiwenlei@whu.edu.cn

过渡金属催化的不对称环异构化反应催化活性高、选择性好,被认为是一条符合“原子经济性”的合成途径。近年来,该领域取得了长足的进步,成为构建高官能团活性的手性碳环与杂环化合物的最有效手段之一。本文比较全面地综述了20年来过渡金属催化的1,n-烯炔类化合物的不对称环异构化反应,并简单介绍了该反应在天然产物的合成过程中的应用。

Asymmetric cycloisomerization catalyzed by transition metals, which possesses highly catalytic activity and good selectivity, is a potential protocol to fulfill the goal of “atom economic”.In recent years, impressive achievements have been made in this area. It becomes one of the most efficient methods to synthesize enantiomeric pure carbon- or heterocyclic compounds. This paper summarized the development of transition metal catalyzed asymmetric cycloisomerization in recent twenty years and briefly reviewed its applications in total synthesis of natural products.

Contents 
1 Introduction 
2 Asymmetric cycloisomerization of enynes catalyzed by different transition metals 
2.1 Palladium-catalyzed reactions 
2.2 Rhodium-catalyzed reactions 
2.3 Platinum, gold and iridium-catalyzed reactions 
3 Applications in the syntheses of natural products
3.1 Asymmetric transformation catalyzed by chiral catalysts 
3.2 Asymmetric transformation induced by chiral substrates 
4 Conclusion

()

[1 ] Hudlicky T,Price J D. Chem. Rev. ,1989,89: 1467—1486
[2 ] Trost B M. Chem. Soc. Rev. ,1982,11: 141—170
[3 ] Lautens M,Klute W,Tam W. Chem. Rev. ,1996,96: 49—92
[4 ] Negishi E I,Coperet C,Ma S,et al. Chem. Rev. ,1996,96:
365—393
[5 ] Aubert C,Buisine O,Malacria M. Chem. Rev. ,2002,102:
813—834
[6 ] Tenaglia A,Heumann A. Angew. Chem. Int. Ed. ,1999,38:
2180—2184
[7 ] Dounay A B,Overman L E. Chem. Rev. ,2003,103: 2945—
2963
[8 ] Montgomery J. Angew. Chem. Int. Ed. ,2004,43: 3890—
3908
[9 ] Trost B M. Angew. Chem. Int. Ed. ,1995,34: 259—281
[10] Trost B M. Science,1991,254: 1471—1477
[11] Trost B M,Lautens M. J. Am. Chem. Soc. , 1985, 107:
1781—1783
[12] Trost B M. Acc. Chem. Res. ,1990,23: 34—42
[13] Ojima I,Tzamarioudaki M,Li Z,et al. Chem. Rev. ,1996,
96: 635—662
[14] Fruehauf H W. Chem. Rev. ,1997,97: 523—596
[15] Trost B M,Krische M J. Synlett,1998,1—16
[16] Nakamura I,Yamamoto Y. Chem. Rev. ,2004,104: 2127—
2198
[17] Echavarren A M,Nevado C. Chem. Soc. Rev. ,2004,33:
431—436
[18] Anorbe L,Dominguez G,Perez-Castells J. Chem. Eur. J. ,
2004,10: 4938—4943
[19] Bruneau C. Angew. Chem. Int. Ed. ,2005,44: 2328—2334
[20] Zhang L,Sun J,Kozmin S A. Adv. Synth. Catal. ,2006,348:
2271—2296
[21] Fairlamb I J S. Angew. Chem. Int. Ed. ,2004,43: 1048—
1052
[22] Trost B M,Lee D C,Rise F. Tetrahedron Lett. ,1989,30:
651—654
[23] Trost B M,Czeskis B A. Tetrahedron Lett. ,1994,35: 211—
214
[24] Goeke A,Sawamura M,Kuwano R,Ito Y. Angew. Chem. Int.
Ed. Engl. ,1996,35: 662—663
[25] Zhang Q,Lu X Y. J. Am. Chem. Soc. ,2000,122: 7604—
7605
[26] Zhang Q,Lu X Y,Han X. J. Org. Chem. ,2001,66: 7676—
7684
[27] Hatano M,Terada M,Mikami K. Angew. Chem. Int. Ed. ,
2001,40: 249—253
[28] Hatano M, Mikami K. J. Am. Chem. Soc. , 2003, 125:
4704—4705
[29] Hatano M,Mikami K. J. Mol. Catal. A: Chem. ,2003,196:
165—169
[30] Hatano M,Mikami K. Org. Biomol. Chem. ,2003,1: 3871—
3873
[31] Hatano M,Yamanaka M,Mikami K. Eur. J. Org. Chem. ,
2003,2552—2555
[32] Imase H,Suda T,Shibata Y,et al. Org. Lett. ,2009,11:
1805—1808
[33] Jolly R S,Luedtke G,Sheehan D,et al. J. Am. Chem. Soc. ,
1990,112: 4965—4966
[34] Wender P A,Takahashi H,Witulski B. J. Am. Chem. Soc. ,
1995,117: 4720—4721
[35] Wender P A,Husfeld C O,Langkopf E,et al. J. Am. Chem.
Soc. ,1998,120: 1940—1941
[36] Koga Y,Kobayashi T,Narasaka K. Chem. Lett. ,1998,249—
250
[37] Fairlie D P,Bosnich B. Organometallics,1988,7: 936—945
[38] Tani K,Yamagata T,Akutagawa S,et al. J. Am. Chem. Soc. ,
1984,106: 5208—5217
[39] Crabtree R. Acc. Chem. Res. ,1979,12: 331—337
[40] Park J H,Chang K M,Chung Y K. Coord. Chem. Rev. ,
2009,253: 2461—2480
[41] Perez-Castells J. Topics in Organometallic Chemistry,2006,19:
207—257
[42] Gibson S E,Stevenazzi A. Angew. Chem. Int. Ed. ,2003,42:
1800—1810
[43] Chi Y, Tang W, Zhang X M. Modern Rhodium-Catalyzed
Organic Reactions ( Ed. Evans P A) . Weinheim: Wiley-VCH,
2005. 1—31
[44] Nass A R,Briel O. Chimica Oggi,2003,21: 58—61
[45] Halpern J. Asymmetric Synth. ,1985,5: 41—69
[46] Cao P,Wang B,Zhang X M. J. Am. Chem. Soc. ,2000,122:
6490—6491
[47] Cao P, Zhang X M. Angew. Chem. Int. Ed. ,2000,39:
4104—4106
[48] Lei A W,He M,Wu S,et al. Angew. Chem. Int. Ed. ,2002,
41: 3457—3460
[49] Lei A W,He M,Zhang X M. J. Am. Chem. Soc. ,2002,
124: 8198—8199
[50] Lei A W,Waldkirch J P,He M,et al. Angew. Chem. Int.
Ed. ,2002,41: 4526—4529
[51] Liu F,Liu Q,He M,et al. Org. Biomol. Chem. ,2007,5:
3531—3534
[52] Lei A W,He M,Zhang X M. J. Am. Chem. Soc. ,2003,
125: 11472—11473
[53] He M,Lei A W,Zhang X M. Tetrahedron Lett. ,2005,46:
1823—1826
[54] Hashmi A S K,Haufe P,Nass A R. Adv. Synth. Catal. ,
2003,345: 1237—1241
[55] Hashmi A S K,Haufe P,Nass A R,et al. Adv. Synth. Catal. ,
2004,346: 421—424
[56] Mikami K,Kataoka S,Yusa Y,et al. Org. Lett. ,2004,6:
3699—3701
[57] Mikami K,Yusa Y,Hatano M,et al. Chem. Commun. ,2004,98—99
[58] Nicolaou K C,Li A,Ellery S P,et al. Angew. Chem. Int.
Ed. ,2009,48: 6293—6295
[59] Gilbertson S R,Hoge G S,Genov D G. J. Org. Chem. ,1998,
63: 10077—10080
[60] Mamane V,Gress T,Krause H,et al. J. Am. Chem. Soc. ,
2004,126: 8654—8655
[61] Shibata T,Kobayashi Y,Maekawa S,et al. Tetrahedron,2005,
61: 9018—9024
[62] Brissy D,Skander M,Jullien H,et al. Org. Lett. ,2009,11:
2137—2139
[63] Watson I D G,Ritter S,Toste F D. J. Am. Chem. Soc. ,
2009,131: 2056—2057
[64] Worthen D M, Zimmerman T J, Wind C A. Invest.
Ophthalmol. ,1974,13: 296—299
[65] Wang J,Soisson S M,Young K,et al. Nature,2006,441:
358—361
[66] Singh S B,Jayasuriya H,Ondeyka J G,et al. J. Am. Chem.
Soc. ,2006,128: 11916—11920
[67] Nicolaou K C,Li A,Edmonds D J. Angew. Chem. Int. Ed. ,
2006,45: 7086—7090
[68] Nicolaou K C,Edmonds D J,Li A,et al. Angew. Chem. Int.
Ed. ,2007,46: 3942—3945
[69] Porta A,Vidari G,Zanoni G. J. Org. Chem. ,2005,70:
4876—4878
[70] De Azevedo M B M,Greene A E. J. Org. Chem. ,1995,60:
4940—4942
[71] Vidari G, Lanfranchi G, Sartori P, et al. Tetrahedron:
Asymmetry,1995,6: 2977—2990
[72] Trost B M,Corte J R. Angew. Chem. Int. Ed. ,1999,38:
3664—3666
[73] Trost B M,Corte J R,Gudiksen M S. Angew. Chem. Int. Ed. ,
1999,38: 3662—3664
[74] Allbutt A D,Ayer W A,Brodie H J,et al. Can. J. Microbiol. ,
1971,17: 1401—1407
[75] Ayer W A,Lee S P. Can. J. Chem. ,1979,57: 3332—3337
[76] Trost B M,Dong L,Schroeder G M. J. Am. Chem. Soc. ,
2005,127: 2844—2845
[77] Trost B M,Dong L,Schroeder G M. J. Am. Chem. Soc. ,
2005,127: 10259—10268

[1] 王亚奇, 吴强, 陈俊玲, 梁峰. 狄尔斯-阿尔德反应催化剂[J]. 化学进展, 2022, 34(2): 474-486.
[2] 杨琪, 欧阳昆冰, 刘亮, 席振峰. 三甲基硅基(TMS)化学:C(sp3)-Si键的催化活化[J]. 化学进展, 2018, 30(5): 513-527.
[3] 张宇, 岑竞鹤, 熊文芳, 戚朝荣, 江焕峰*. CO2:羧基化反应的C1合成子[J]. 化学进展, 2018, 30(5): 547-563.
[4] 阙楚强, 陈宁*, 许家喜*. 氨基甲酸酯在C—H键活化中的应用[J]. 化学进展, 2018, 30(2/3): 139-155.
[5] 熊兴泉, 范观铭, 朱荣俊, 石霖, 肖上运, 毕成. 酰胺类化合物的高效合成研究[J]. 化学进展, 2016, 28(4): 497-506.
[6] 龚浩, 杨义文, 匡春香. 基于C—H键官能团化的药物合成[J]. 化学进展, 2014, 26(04): 592-608.
[7] 戚自松, 董亚丽, 李亚明*, 段春迎* . 过渡金属催化芳香化合物三氟甲基化反应[J]. 化学进展, 2012, 24(11): 2177-2186.
[8] 刘冠男, 周宇, 蒋华良, 柳红. 银催化的有机合成反应[J]. 化学进展, 2011, 23(6): 1137-1147.
[9] 姚臻 戴斌斌 刘少杰 曹堃 傅建松 谢家明. 乙烯和降冰片烯加成共聚合催化体系*[J]. 化学进展, 2010, 22(10): 2024-2032.
[10] 马欣 范为正 李晓明 姚莹 张兆国. 无溶剂条件下的不对称催化反应[J]. 化学进展, 2010, 22(07): 1310-1340.
[11] 王春翔 李新成 徐粉 万伯顺. 过渡金属催化[2 + 2 + 2]环加成反应合成吡啶衍生物[J]. 化学进展, 2010, 22(04): 610-630.
[12] 卢玉华 宋飞杰 贾学顺 刘元红. 过渡金属催化的呋喃合成*[J]. 化学进展, 2010, 22(01): 58-70.
[13] 李旭琴 刘安. 无保护基法合成的启示*[J]. 化学进展, 2010, 22(01): 81-90.
[14] 郑欣,王永梅. 脯氨酸催化的不对称有机反应[J]. 化学进展, 2008, 20(11): 1675-1686.
[15] 姚成福,孙彩霞,闫少宇,吴海虹. 手性咪唑啉酮类有机催化剂催化的不对称反应*[J]. 化学进展, 2008, 20(06): 887-898.