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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (08): 1059-1065. 上一篇    下一篇

综述与进展

含硅路易斯酸的发展及其在有机合成中的应用

唐子龙1,2   

  1. (1湖南科技大学化学化工学院 湘潭 411201)
    (2 Department of Chemistery, University of Louvain, l Place Louis Pasteur B-1348 Louvain-la-neuve Belgique)
  • 收稿日期:2005-12-08 修回日期:2006-06-15 发布日期:2006-07-26
  • 通讯作者: 唐子龙

Development of Silicon-Based Lewis Acids and Their Applications to Organic Synthesis

TANG Zi-Long1,2   

  1. (1 School of Chemistry and Chemical Engineering, Hunan University of Science and Tech-nology, Xiangtan 411201)
    (2 Department of Chemistery, University of Lou-vain, 1 Place Louis Pasteur B-1348 Louvain-la-neuve Belgique)
  • Received:2005-12-08 Revised:2006-06-15 Published:2006-07-26
  • Contact: TANG Zi-Long

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综述了含硅路易斯酸R3SiX [X＝I, OTf, NTf2, C(C6F5)Tf2等]和(R3SiX＋MLn)的发展、合成以及它们在有机合成中的应用. 它们主要被用来催化Aldol, 烯丙基化, Diels-Alder, Ene和Friedel-Crafts等反应. 催化剂的用量一般为0.5～20 mol%, 并随着催化剂的活性不同, 反应产率从一般到良好不等. 催化剂活性顺序为R3SiNTf2＞R3SiOTf, (R3SiX＋MLn)＞R3SiX. 也对近年出现的手性含硅路易斯酸的发展和应用进行了概述, 当手性双-(多氟甲磺酰)-亚胺基硅烷用于催化环戊二烯和丙烯酸甲酯的Diels-Alder反应时, ee值高达54%.

关键词: (手性)含硅路易斯酸, 发展, 合成, 应用

This paper mainly describes the development, synthesis and applications of silicon-based Lewis acids R3SiX [X＝I, OTf, NTf2, C(C6F5)Tf2, etc.] and (R3SiX＋MLn). They were principally used to catalyze aldol, allylation, Diels-Alder, ene and Friedel-Crafts reactions. SLAs were used in 0.5～20 mol%, and the yields of the catalyzed reactions varied from moderate to excellent with the different reactivity of silicon-based Lewis acids. The order of the reactivities is R3SiNTf2＞R3SiOTf, (R3SiX＋MLn)＞R3SiX. The development and applications of chiral SLAs are also reviewed. When chiral trialkylsilyl bis(perfluoromethanesulfonyl)imides were used as catalysts for Diels-Alder reaction of cyclopentadiene and methyl acrylate, ee value of the reaction was up to 54%.

Key words: application, development, synthesis, (chiral) silicon-based Lewis acid