The search for tolerant Lewis acid catalysts. Part 1: Chiral silicon Lewis acids derived from (-)-myrtenal
(2000) Tetrahedron Letters — Vol. 41, n° 49, p. 9561-9564 (2000)
Files
pdfdocument.pdf
Restricted Access - Adobe PDF
- 70.46 KB
Details
- Authors
- Abstract
- 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.
- Affiliations
Citations
Mathieu, B., de Fays, L., & Ghosez, L. (2000). The search for tolerant Lewis acid catalysts. Part 1: Chiral silicon Lewis acids derived from (-)-myrtenal. Tetrahedron Letters, 41(49), 9561-9564. https://doi.org/10.1016/S0040-4039(00)01694-4 (Original work published 2000)