A Palladium-Catalyzed Asymmetric Allylic Alkylation Approach to α-Quaternary γ-Butyrolactones.

Org Lett

Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI) - ESPCI Paris/CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France.

Published: January 2017

AI Article Synopsis

  • A new method called Pd-catalyzed asymmetric allylic alkylation (Pd-AAA) is introduced, which uses enol carbonates from γ-butyrolactones.
  • This technique produces α,α'-disubstituted γ-butyrolactones with high yields and enantioselectivities, achieving up to 94% enantiomeric excess (ee).
  • The method has also been successfully utilized to create chiral spirocyclic compounds.

Article Abstract

The Pd-catalyzed asymmetric allylic alkylation (Pd-AAA) of enol carbonates derived from γ-butyrolactones is reported, affording the corresponding enantioenriched α,α'-disubstituted γ-butyrolactones in both high yields and high enantioselectivities (up to 94% ee). This method was eventually applied to the synthesis of chiral spirocyclic compounds.

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Source
http://dx.doi.org/10.1021/acs.orglett.6b02971DOI Listing

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