English
往期目录
新闻公告
More
化学进展 2008, Vol. 20 Issue (10): 1544-1552 前一篇   后一篇

• 综述与评论 •

烯酮中间体及其在不对称环加成反应中的应用

方钊 唐瑞仁* 罗佐文   

  1. （中南大学化学化工学院 长沙 410083）

  • 收稿日期:2007-11-27 修回日期:2008-03-12 出版日期:2008-10-24 发布日期:2008-10-25
  • 通讯作者: 唐瑞仁
下载PDF ( 1916 ) 引用
导出 被引次数 ( 6 | 1 )

Ketene intermediates and their Application in Asymmetric Cycloaddition Reaction

Fang Zhao; Tang Ruiren*; Luo Zuowen   

  1. (School of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China )
  • Received:2007-11-27 Revised:2008-03-12 Online:2008-10-24 Published:2008-10-25
  • Contact: Tang Ruiren
烯酮作为一种重要的中间体在有机合成中具有非常广泛的应用，本文主要对烯酮中间体的结构与制备及近年来烯酮与醛或亚胺的[2+2]环加成反应以及与活泼不饱和双键的[2+2]或[4+2]环加成反应在不对称有机合成中的应用进展作一综述，包括不同催化剂对反应的立体选择性控制及其反应机理。
关键词： 烯酮, 环加成反应, 不对称合成
Ketenes have very broad applied scope as an important intermediate in organic synthesis. This paper mainly reviews the structure and preparation of ketene intermediates, the recent advance in asymmetric organic synthesis application of ketene intermediates in [2+2] cycloaddition reactions with aldehyde and imine, as well as in [2+2] and [4+2] cycloaddition reactions with active unsaturated double-bonds, including the reaction stereoselective controlling and mechanism using different catalysts.
Key words: ketenes, cycloaddition, asymmetric synthesis

中图分类号: 

()

[ 1 ] Tidwell T T. Acc. Chem. Res. , 1990 , 23 : 273 —279
[ 2 ] Woodward R B , Hoffmann R. The Conservation of Orbital Symmetry. New York : Verlag Press , 1969
[ 3 ] Tidwell T T. Tetrahedron Lett . , 1979 , 20 : 4615 —4618
[ 4 ] Nguyen M T , Hegarty A F. J . Am. Chem. Soc. , 1984 , 106 :1552 —1557
[ 5 ] Houk K N , Strozier R W, Hall J A. Tetrahedron Lett . , 1974 ,15 : 897 —900
[ 6 ] Firl J , Runge W Z. Naturforsch , 1974 , 29B : 393 —398
[ 7 ] Duncan J L , Munro B J . Mol . Struct . , 1987 , 161 : 311 —319
[ 8 ] Tanaka K, Yoshimine M. J . Am. Chem. Soc. , 1980 , 102 :7655 —7662
[ 9 ] Bouma W J , Nobes R H , Radom L , et al . J . Org. Chem. ,1982 , 47 : 1869 —1875
[10] Seikaly H R , Tidwell T T. Tetrahedron , 1986 , 42 : 2587 —2613
[11] Gong L Y, Mcallister M A , Tidwell T T. J . Am. Chem. Soc. ,1991 , 113 : 6021 —6028
[12] Libby M C , Watson P C , Barteau MA. Ind. Eng. Chem. Res. ,1994 , 33 : 2904 —2912
[13] Masters A P , Sorenson T S , Ziegler T. J . Org. Chem. , 1986 ,51 : 3558 —3559
[14] Miyashita A , Shitara H , Nohira H. Organometallics , 1985 , 4 :1463 —1466
[15] Olah GA , Wu A H , Faroop O. Synthesis , 1989 , 568 —568
[16] Bonini B F , Femoni C , Comes-Franchini M, et al . Synlett ,2001 , 1092 —1096
[17] Cevasco G, Vigo D , Thea S. J . Org. Chem. , 2000 , 65 : 7833 —7838
[18] Cho B R , Jeong H C , Seong Y J , et al . J . Org. Chem. , 2002 ,67 : 5232 —5238
[19] Nahmany M, Melman A. Org. Lett . , 2001 , 3 : 3733 —3735
[20] Shelkov R , Nahmany M, Melman A. J . Org. Chem. , 2002 , 67 :8975 —8982
[21] Shelkov R , Nahmany M, Melman A. Org. Biomol . Chem. ,2004 , 2 : 397 —401
[22] Wiskur S L , Fu GC. J . Am. Chem. Soc. , 2005 , 127 : 6176 —6177
[23] Allen A D , Cheng B , Fenwick M H , et al . Org. Lett . , 1999 , 1 :693 —696
[24] Allen A D , Andraos J , Kresge AJ , Mcallister MA , Tidwell T T.J . Am. Chem. Soc. , 1992 , 114 : 1878 —1879
[25] Allen A D , Kresge A J , Schepp N P , Tidwell T T. Can. J .Chem. , 1987 , 65 : 1719 —1723
[26] Chiang Y, Fedorov A V , Kresge A J , et al . J . Am. Chem.Soc. , 2004 , 126 : 9382 —9386
[27] Nils P , Lotta J , Fredrik A. Org. Lett . , 2006 , 8 : 935 —938
[28] Nelson S G, Wan Z H , Peelen T J , et al . Tetrahedron Letters ,1999 , 40 : 6535 —6539
[29] Tamai Y, Someya M, Fukumoto J , et al . J . Chem. Soc. Perkin.Trans. , 1994 , 1549 —1550
[30] Tamai Y, Yoshiwara H , Someya M, et al . J . Chem. Soc. Chem.Commun. , 1994. 2281 —2282
[31] Dymock B W, Kocienski P J , Pons J M. J . Chem. Soc. Chem.Commun. , 1996 , 1053 —1054
[32] Romo D , Harrision P H , Jenkins S I , et al . Bioorg. Med.Chem. , 1998 , 6 : 1255 —1272
[33] Zipp G G, Hikifiker M A , Nelson S G. Org. Lett . , 2002 , 4 :1823 —1826
[34] Nelson S G, Kim B K, Peelen T J . J . Am. Chem. Soc. , 2000 ,122 : 9318 —9319
[35] Nelson S G, Peelen T J , Wan Z H. Tetrahedron Lett . , 1999 ,40 : 6541 —6543
[36] Nelson S G, Zhu C , Shen X Q. J . Am. Chem. Soc. , 2004 ,126 : 14 —15
[37] Zhu C , Shen X Q , Nelson S G. J . Am. Chem. Soc. , 2004 ,126 : 5352 —5353
[38] Wynberg H , Staring E GJ . J . Org. Chem. , 1985 , 50 : 1977 —1979
[39] Shen X Q , Wasmuth A S , Zhao J , et al . J . Am. Chem. Soc. ,2006 , 128 : 7438 —7439
[40] Cortez G S , Tennyson R L , Romo D. J . Am. Chem. Soc. ,2001 , 123 : 7945 —7946
[41] Calter M A , Orr R K, Song W. Org. Lett . , 2003 , 5 : 4745 —4748
[42] Purohit V C , Richardson R D , Smith J W, et al . J . Org.Chem. , 2006 , 71 : 4549 —4558
[43] Paolo S T , Rene P. Angew. Chem. Int . Ed. , 2007 , 46 : 5325 —5328
[44] Gnanadesikan V , Corey E J . Org. Lett . , 2006 , 8 : 4943 —4945
[45] Nagai D , Sudo A , Endo T. Macromolecules , 2006 , 39 : 8898 —8900
[46] Merlic C A , Doroh B C. J . Org. Chem. , 2003 , 68 : 6056 —6059
[47] Evans D A , Sjogren E B. Tetrahedron lett . , 1985 , 26 : 3783 —3786
[48] Matsui S , Hashimoto Y, Saigo K. Synthesis , 1998 , 1161 —1166
[49] Saul R , Kopf J , Kêll P. Tetrahedron Asymmetry , 2000 , 423 —433
[50] Taggi A E , Wack H , Hafez A M, et al . Org. Lett . , 2002 , 4 :627 —629
[51] Hafez A M, Taggi A E , Dudding T , Leckta T. J . Am. Chem.Soc. , 2001 , 123 : 10853 —10859
[52] France S , Wack H , Leckta T J , et al . Org. Lett . 2002 , 4 :1603 —1605
[53] Taggi A E , Hafez A M, Wack H , Lectka T , et al . J . Am.Chem. Soc. , 2002 , 124 : 6626 —6635
[54] Abraham C J , Paull D H , Scerba M T , et al . J . Am. Chem.Soc. , 2006 , 128 : 13370 —13371
[55] Xu X, Wang K, Nelson S G. J . Am. Chem. Soc. , 2007 , 129 :11690 —11691
[56] Hodous B L , Fu GC. J . Am. Chem. Soc. , 2002 , 124 : 1578 —1579
[57] Lee E C , Hodous B L , Fu G C , et al . J . Am. Chem. Soc. ,2005 , 127 : 11586 —11587
[58] Liang Y, Jiao L , Zhang S W, Xu J . J . Org. Chem. , 2005 , 70 :334 —337
[59] Hegedus L S. Acc. Chem. Res. , 1995 , 28 : 299 —305
[60] Pemberton N , Emtenas H , Bostrom D , et al . Org. Lett . , 2005 ,7 : 1019 —1021
[61] Emtenas H , Alderin L , Almqvist F. J . Org. Chem. , 2001 , 66 :6756 —6761
[62] Macias A , Alonso E , del Pozo C , et al . J . Org. Chem. , 2004 ,69 : 7004 —7012
[63] Cremonesi G, Croce P D , Rosa C L. Tetrahedron , 2004 , 60 :93 —97
[64] Ma C , Ding H F , Wang Y G. Org. Lett . , 2006 , 8 : 3133 —3136
[65] Machiguchi T , Okamoto J , Morita Y, et al . J . Am. Chem.Soc. , 2006 , 128 : 44 —45
[66] Machiguchi T , Okamoto J , Takachi J , et al . J . Am. Chem.Soc. , 2003 , 125 : 14446 —14448
[67] Zhou C , Birney D M. J . Am. Chem. Soc. , 2002 , 124 : 5231 —5241
[68] Coleman R S , Fraser J R. J . Org. Chem. , 1993 , 58 : 385 —392
[69] Saidi K, Shaterian H , Aghaei D. Heterocycl . Commun. , 2000 ,6 : 93 —95
[70] Bekele T , Shah M H , Wolfer J , et al . J . Am. Chem. Soc. ,2006 , 128 : 1810 —1811
[71] Avenoza A , Busto J H , Canal N , Peregrina J M. Chem.Commun. , 2003 , 1376 —1377
[72] Allen A D , GongL Y, Tidwell T T. J . Am. Chem. Soc. , 1990 ,112 : 6396 —6397
[73] Machiguchi T , hasegawa T , Ishiwata A , et al . J . Am. Chem.Soc. , 1999 , 121 : 4771 —4786
[74] Ussing B R , Hang C , Singleton D A. J . Am. Chem. Soc. ,2006 , 128 : 7594 —7607
[75] Robertson J , Fowler T G. Org. Biomol . Chem. , 2006 , 4 :4307 —4318
[76] Bélanger G, Lévesque F , Páquet J , et al . J . Org. Chem. ,2005 , 70 : 291 —296
[1] 曹如月, 肖晶晶, 王伊轩, 李翔宇, 冯岸超, 张立群. 杂Diels-Alder 环加成反应级联RAFT聚合[J]. 化学进展, 2023, 35(5): 721-734.
[2] 董军, 许家喜. 烯亚砜化合物的制备及反应概述[J]. 化学进展, 2022, 34(5): 1088-1108.
[3] 廖伊铭, 吴宝琪, 唐荣志, 林峰, 谭余. 环张力促进的叠氮-炔环加成反应[J]. 化学进展, 2022, 34(10): 2134-2145.
[4] 章强, 黄文峻, 王延斌, 李兴建, 张宜恒. 基于铜催化叠氮-炔环加成反应的聚氨酯功能化[J]. 化学进展, 2020, 32(2/3): 147-161.
[5] 孔令斌, 严胜骄*, 林军*. 杂环烯酮缩胺:构筑分子多样性稠杂环化合物的合成先导分子[J]. 化学进展, 2018, 30(5): 639-657.
[6] 丁奇峰, 杨雅琼, 缪文俊, 黄和, 于杨*, 黄菲*. 基于N,S-缩烯酮的杂环合成的研究[J]. 化学进展, 2018, 30(11): 1615-1623.
[7] 白东亚, 何军邀, 欧阳斌, 黄金, 王普. 手性芳基醇的生物催化不对称合成[J]. 化学进展, 2017, 29(5): 491-501.
[8] 何桥, 殷中琼, 陈华保, 张祖民, 王显祥, 乐贵洲. 茚及其衍生物的催化不对称合成[J]. 化学进展, 2016, 28(6): 801-813.
[9] 方德彩*. [2+2]环加成反应机理的理论研究[J]. 化学进展, 2012, 24(06): 879-885.
[10] 杨绳岩, 吴振奕, 万新军, 晏娟. 卟啉-富勒烯络合物的合成[J]. 化学进展, 2011, 23(6): 1123-1136.
[11] 刘湘, 潘争光, 许建和. 手性芳基邻二醇的不对称合成[J]. 化学进展, 2011, 23(5): 903-913.
[12] 方玲 石岩 朱成建. 有机小分子催化的β-酮酯不对称α-官能化反应[J]. 化学进展, 2010, 22(09): 1679-1686.
[13] 朱映光 翟昌伟 胡文浩. 不对称多组分反应[J]. 化学进展, 2010, 22(07): 1380-1396.
[14] 李楠 刘伟军 龚流柱. 手性有机小分子催化的最新进展*[J]. 化学进展, 2010, 22(07): 1362-1379.
[15] 王春,刘伟华,周欣,李越敏,李云鹏. 有机催化不对称[4+2]环加成反应*[J]. 化学进展, 2009, 21(09): 1857-1868.