SIOC English
有机化学
高级检索

有机化学 ›› 2009, Vol. 29 ›› Issue (04): 653-657. 上一篇    下一篇

研究简报

新手性双-(三氟甲磺酰)亚胺基硫代缩酮基硅烷的合成及其不对称催化Diels-Alder反应

唐子龙   

  1. (a湖南科技大学化学化工学院 分子构效关系湖南省高校重点实验室 湘潭 411201)
    (b Laboratoire de Chimie Organique de Synthèse, Université catholique de Louvain, Place Louis Paster 1,
    B-1348 Louvain-la -Neuve, Belgium)
  • 收稿日期:2008-10-17 修回日期:2008-11-11 发布日期:2009-04-20
  • 通讯作者: 唐子龙

Synthesis of Novel Chiral Bis-(trifluoromethylsulfonyl)imidyl Dithioketal Silanes and Their Applications to Asymmetric Diels-Alder Reactions

Tang, Zilong   

  1. (a Hunan Provincial University Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering,
    Hunan University of Science and Technology, Xiangtan 411201)
    (b Laboratoire de Chimie Organique de Synthèse, Université catholique de Louvain, Place Louis Paster 1,
    B-1348 Louvain-la-Neuve, Belgium)
  • Received:2008-10-17 Revised:2008-11-11 Published:2009-04-20
  • Contact: Tang, Zilong

PDF

1513

被引次数

8

合成了数个新手性双-(三氟甲磺酰)亚胺基二硫代缩酮基硅路易斯酸2～4, 并研究了它们对环戊二烯和丙烯酸衍生物11a～11c的Diels-Alder反应的催化活性. 结果表明催化剂活性高, 环加成反应的产率高达89%～96%, 并且获得较高的非对映选择性和中等对映选择性, 当催化剂为2b时, 反应的对映选择性达到最高, 为48% ee.

关键词: 手性硅路易斯酸, 不对称催化反应, Diels-Alder反应

A few of new chiral bis-(trifluoromethylsulfonyl)imidyl dithioketal silanes 2～4 were prepared, and used as catalysts for Diels-Alder reactions of cyclopentadiene with acrylic acid derivatives 11a～11c. The results showed that these catalysts were very efficient by high yields (89%～96%), good diastereoselectivity and moderate enantioselectivity of the catalyzed cyclic additions. The ee values of the cyclic addition reactions were up to 48% when compound 2b was used as catalyst.

Key words: chiral silicon-based Lewis acid, asymmetric catalysis reaction, Diels-Alder reaction