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Updated: Jun 21, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Highly diastereoselective three-component vinylogous Mannich reaction between isoquinolines, acyl/sulfonyl chlorides,
Philippe Hermange1, Marie Elise Tran Huu Dau, Pascal Retailleau
1Institut de Chimie des Substances Naturelles - CNRS UPR 2301, Gif-sur-Yvette, France.
Abstract:
Reaction of an isoquinoline, a silyloxyfuran, and an acyl or sulfonyl chloride provides easy access to a wide variety of isoquinolinobutyrolactones with excellent yields and diastereoselectivites (R*,R* isomer), even in the case of formation of quaternary centers (i.e., R(3) or R(4) = Me). Moreover, the use of a chiral auxiliary allowed formation of a single stereoisomer in 96% yield. This represents the first examples of asymmetric vinylogous Mannich reactions on isoquinolinium salts.
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