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

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (04): 653-657. Previous Articles Next Articles

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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

(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

(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

Abstract

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

Cite this article

Tang, Zilong. Synthesis of Novel Chiral Bis-(trifluoromethylsulfonyl)imidyl Dithioketal Silanes and Their Applications to Asymmetric Diels-Alder Reactions[J]. Chin. J. Org. Chem., 2009, 29(04): 653-657.

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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

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

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