Catalytic Dynamic Kinetic Resolutions with N-heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β-lactones

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2012 Jun 16

PMID 22700327

Citations 16

Authors

Daniel T Cohen

Chad C Eichman

Eric M Phillips

Emily R Zarefsky

Karl A Scheidt

Affiliations

Soon will be listed here.

Abstract

New DKR type: An N-heterocyclic carbene (NHC)-catalyzed dynamic kinetic resolution of racemic α-substituted β-keto esters has been developed. This method relies on the epimerization of an NHC-enol intermediate before subsequent aldol/acylation events. Highly substituted β-lactones are produced in good yield with good to excellent selectivities (see scheme).

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