Rapid Generation of Molecular Complexity: Synthesis of α-Hydroxyallenes Using Functionalized Grignard Reagents

Abstract

The use of functionalized aryl-Grignard reagents in the copper-mediated S N 2′ substitution of propargylic oxiranes leads to structurally complex α-hydroxyallenes, usually with high yield and diastereoselectivity. Further transformations, such as gold-catalyzed cycloisomerization to 2,5-dihydrofurans and palladium-catalyzed coupling reactions, demonstrate the high potential of these compounds for the rapid generation of molecular complexity.