Tetrahedron Letters p. 9561 - 9564 (2000)
Update date:2022-07-30
Topics:
Mathieu
De Fays
Ghosez
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.
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