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Stereodivergent synthesis of 2-alkynyl buta-1,3-dienes using Sonogashira coupling with controllable retention or inversion of olefin geometry

Abstract A stereodivergent approach to 2-alkynyl buta-1,3-dienes from a single stereoisomer of starting α-bromoenal has been developed. By simply switching the sequence of Sonogashira and Horner-Wadsworth-Emmons reactions, it is possible… Click to show full abstract

Abstract A stereodivergent approach to 2-alkynyl buta-1,3-dienes from a single stereoisomer of starting α-bromoenal has been developed. By simply switching the sequence of Sonogashira and Horner-Wadsworth-Emmons reactions, it is possible to obtain these branched dienynes with retention or almost complete inversion of the double bond configuration.

Keywords: alkynyl buta; retention; geometry; buta dienes

Journal Title: Tetrahedron Letters
Year Published: 2020

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