Efficient Synthesis of 3-Alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-ones by a Stork–Danheiser Sequence from Vinylogous Esters and Terminal Alkynes

Abstract

An efficient Stork–Danheiser sequence has been developed for the preparation of a variety of 3-alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-ones in good to excellent yields from the corresponding 4,6,7,8-tetrahydro-5H-1,3-benzodioxin-5-ones and terminal alkynes. Several of the 3-alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-one products were catalytically cyclized to give the corresponding 3-aryl-1,5,6,7-tetrahydro-8H-isochromen-8-ones.

Key words

alkynylations - Stork–Danheiser sequences - vinylogous esters - alkynes - cyclizations - chromenones

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