A Sequential Umpolung/Enzymatic Dynamic Kinetic Resolution Strategy for the Synthesis of γ-Lactones

Mark A. Maskeri, Malte L. Schrader, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Combining biological and small-molecule catalysts under a chemoenzymatic manifold presents a series of significant advantages to the synthetic community. We report herein the successful development of a two-step/single flask synthesis of γ-lactones through the merger of Umpolung catalysis with a ketoreductase-catalyzed dynamic kinetic resolution, reduction, and cyclization. This combined approach delivers highly enantio- and diastereoenriched heterocycles and demonstrates the feasibility of integrating NHC catalysis with enzymatic processes.

Original languageEnglish (US)
Pages (from-to)5794-5798
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number26
DOIs
StatePublished - May 7 2020

Keywords

  • N-heterocyclic carbene catalysis
  • chemoenzymatic catalysis
  • ketoreductase enzyme
  • photoredox catalysis
  • sequential catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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