Deracemization of Quaternary Stereocenters by Pd‐Catalyzed Enantioconvergent Decarboxylative Allylation of Racemic β‐Ketoesters

2005/10/05 by Justin T. Mohr, Douglas C. Behenna, Andrew M. Harned +1 · 3 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Catalytic C–H Functionalization Methods #Asymmetric Hydrogenation and Catalysis

paper · doi:10.1002/anie.200502018

openalex publication_date 2005/10/05 · openalex created_date 2016/06/24 · openalex updated_date 2026/06/26

Abstract

Stereochemical alchemy! Racemic allyl β-ketoesters allow the regiocontrolled formation of enolates, where the same catalyst is intimately involved in both the stereoablative (CC bond-breaking) and stereoselective (CC bond-forming) steps. This mechanistic and practical insight led to the formation of multiple quaternary carbon stereocenters in a single cascade reaction (see scheme).

Cited by

• Enantioselective Palladium‐Catalyzed Decarboxylative Allylic Alkylations
• Enantioselective Decarboxylative Alkylation Reactions: Catalyst Development, Substrate Scope, and Mechanistic Studies
• Carroll rearrangement [wikipedia]