Unanticipated silyl transfer in enantioselective α,β-unsaturated acyl ammonium catalysis using silyl nitronates

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

Research output: Contribution to journalArticlepeer-review

7 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
JournalOrganic Letters
VolumeArticle ASAP
Early online date23 Dec 2019
DOIs
Publication statusE-pub ahead of print - 23 Dec 2019

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