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

Authors
Mathieu, B de Fays, L Ghosez, L
Citation
B. Mathieu et al., The search for tolerant Lewis acid catalysts. Part 1: Chiral silicon Lewisacids derived from (-)-myrtenal, TETRAHEDR L, 41(49), 2000, pp. 9561-9564
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
49
Year of publication
2000
Pages
9561 - 9564
Database
ISI
SICI code
0040-4039(200012)41:49<9561:TSFTLA>2.0.ZU;2-T
Abstract
We have shown that association of a bulky silicon group with the bis(triflu oromethallesulfonyl)imide leaving group unexpectedly enhances the electroph ilic character of the R3SiNTf2 silylating agent. The presence of a chiral s ubstituent derived from (-)-myrtenal on the silicon atom led to a Lewis aci d, which efficiently catalyzes the Diels-Alder reaction of alpha,beta -unsa turated esters. Although not yet preparatively useful, the enantiomeric exc esses (up to 54%) were the highest ever reported for a chiral silicon Lewis acid. (C) 2000 Elsevier Science Ltd. All rights reserved.