S_N1‐Type Reactions in the Presence of Water: Indium(III)‐Promoted Highly Enantioselective Organocatalytic Propargylation of Aldehydes

Abstract

Water under troubled chemistry! The first catalytic stereoselective addition of aldehydes to internal functionalized propargylic alcohols promoted by a combination of organocatalysis and indium triflate is described (see scheme). The reaction is tolerant of functional groups (FG) and was performed in the presence of water. High enantioselectivities (anti, 92–99 % ee) and moderate diastereomeric ratios (d.r., up to 6.7:1 for the anti isomer) were obtained.