The search for tolerant Lewis acid catalysts. Part 1: Chiral silicon Lewis acids derived from (-)-myrtenal

被引：56

作者：

Mathieu, B

de Fays, L

Ghosez, L

机构：

[1] Catholic Univ Louvain, Lab Chim Organ Synth, B-1348 Louvain, Belgium

[2] ENSCPB, Inst Europeen Chim & Biol, F-33402 Talence, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 49期

关键词：

Lewis acid; silylation; asymmetric Diels-Alder reaction;

D O I：

10.1016/S0040-4039(00)01694-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have shown that association of a bulky silicon group with the bis(trifluoromethallesulfonyl)imide leaving group unexpectedly enhances the electrophilic character of the R3SiNTf2 silylating agent. The presence of a chiral substituent derived from (-)-myrtenal on the silicon atom led to a Lewis acid, which efficiently catalyzes the Diels-Alder reaction of alpha,beta -unsaturated esters. Although not yet preparatively useful, the enantiomeric excesses (up to 54%) were the highest ever reported for a chiral silicon Lewis acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9561 / 9564

页数：4

共 19 条

[1] CHEMISTRY OF METHYLNORBORNYL CATIONS .6. STEREOCHEMISTRY OF VICINAL HYDRIDE SHIFT . EVIDENCE FOR NONCLASSICAL STRUCTURE OF 3-METHYL-2-NORBORNYL CATIONS [J].