303213-92-5Relevant academic research and scientific papers
The search for tolerant Lewis acid catalysts. Part 1: Chiral silicon Lewis acids derived from (-)-myrtenal
Mathieu,De Fays,Ghosez
, p. 9561 - 9564 (2000)
We have shown that association of a bulky silicon group with the bis(trifluoromethanesulfonyl)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 α,β-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.
