TRITYL PERCHLORATE CATALYZED TANDEM MICHAEL–ALDOL REACTION. A FACILE METHOD FOR THE STEREOSELECTIVE SYNTHESES OF γ-ACYL SUBSTITUTED δ-HYDROXY KETONE DERIVATIVES

5 February 1986

journal article
research article
Published by Oxford University Press (OUP) in Chemistry Letters

Vol. 15 (2) , 221-224
https://doi.org/10.1246/cl.1986.221

Abstract

In the presence of a catalytic amount of trityl perchlorate, the intermediate adducts, produced in situ by the conjugate addition of silyl enol ethers with α,β-unsaturated ketones, react with aldehydes to give the corresponding γ-acyl substituted δ-hydroxy ketone derivatives stereoselectively in high yields. The ketones thus obtained are easily converted to tetrahydropyran derivatives.

Keywords

This publication has 2 references indexed in Scilit:

Highly Stereoselective Aldol Condensation Using an Enantioselective Chiral Enolate
Angewandte Chemie International Edition in English, 1980
Organometallic reagents in organic synthesis—V
Tetrahedron, 1979