Unanticipated Silyl Transfer in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis Using Silyl Nitronates

Anastassia Matviitsuk, Mark D. Greenhalgh, James E. Taylor, Xuan B. Nguyen, David B. Cordes, Alexandra M.Z. Slawin, David W. Lupton, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The use of silyl nitronates is reported for the isothiourea-catalyzed synthesis of γ-nitro-substituted silyl esters containing up to two contiguous stereocenters in good yields with excellent enantioselectivities (up to 93% yield and 99:1 er). The serendipitously discovered formation of silyl ester products in this reaction demonstrates a novel platform for catalyst turnover in α,β-unsaturated acyl ammonium catalysis.

Original languageEnglish
Pages (from-to)335-339
Number of pages5
JournalOrganic Letters
Volume22
Issue number1
Early online date23 Dec 2019
DOIs
Publication statusPublished - 3 Jan 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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