A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters

Kathleen J.R. Murauski, Daniel M. Walden, Paul Ha Yeon Cheong, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A general and enantioselective N-heterocyclic carbene (NHC)-catalyzed lactonization of simple enals and α-ketoesters has been discovered using a new ternary cooperative catalytic system. The highly selective annulation was achieved by using a combination of a chiral NHC, a hydrogen-bond donor, and a metal salt, facilitating self-assembly of the reactive partners. A proposed model for this new mode of NHC chiral relay catalysis is supported by experimental and computational mechanistic studies. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)3713-3719
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number21
DOIs
StatePublished - Nov 10 2017

Keywords

  • N-heterocyclic carbene
  • NHC
  • Umpolung
  • cooperative catalysis
  • homoenolate
  • lactone
  • ternary catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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