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Triarylcarbenium ions as catalysts in the Mukaiyama Aldol addition: A mechanistic investigation
Journal article   Peer reviewed

Triarylcarbenium ions as catalysts in the Mukaiyama Aldol addition: A mechanistic investigation

Scott E. Denmark and Chien-Tien Chen
Tetrahedron Letters, Vol.35(25), pp.4327-4330
20/06/1994

Abstract

Aldol Condensation Diastereoselective Triarylcarbenium ions
1-Phenyl-2:3,6:7-dibenzosuberyl salts 5 + efficiently catalyze the aldol reaction between silyl enol ethers and benzaldehyde with moderate diastereoselectivity. Crossover experiments with doubly labeled silyl enol ethers, kinetic and stereochemical studies identify 5 + as the catalyst rather than a Lewis acidic R 3 SiX species in this transformation. © 1994.

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