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

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4 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
DOIs
Publication statusPublished - 3 Jan 2020

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