Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Protected Benzoin-Derived Enol Carbonates

Adv Synth Catal. 2020 Jan 23;362(2):344-347. doi: 10.1002/adsc.201901281. Epub 2019 Nov 5.

Abstract

The enantioselective palladium-catalyzed decarboxylative allylic alkylation of fully substituted α-hydroxy acyclic enol carbonates providing tetrasubstituted benzoin derivatives is reported. Investigation into the transformation revealed that preparation of the starting material as a single enolate isomer is crucial for optimal enantioselectivity. The obtained alkylation products contain multiple reactive sites that can be utilized toward the synthesis of stereochemically rich derivatives. COMMUNICATION.

Keywords: allylic alkylation; asymmetric catalysis; benzoin; palladium catalysis.