Flexible Tetrahydropyran Synthesis from Homopropargylic Alcohols Using Sequential Pd-Au Catalysis

Abstract

A flexible synthetic method toward highly :substituted tetrahydropyran is reported: The key transformation involves atom-efficient sequential metal catalysis, consisting of Pd-catalyzed addition of homopropargylic alcohols to alkoxyallene and the subsequent gold(I)-catalyzed cycloisomerization. Notably, this method gives access to, both 2,6-cis- and 2,6-trans-tetrahydropyrans possessing diverse substitution patterns.