Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones.Org Lett. 2016 Jan 15; 18(2):260-3.OL
The first catalytic asymmetric vinylogous aldol reaction of activated allyls to activated acyclic ketones is disclosed. A variety of activated acyclic ketones, such as trifluoromethyl ketones, α-ketoesters, and α-keto phosphonates, were found to be involved forming diverse γ-selective aldol adducts with high enantioselectivities (up to >99% ee). The method provides an effective, general strategy to access valuable chiral electron-withdrawing group-substituted tertiary hydroxyl-based carboxylic acids.