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

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

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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
Publication statusE-pub ahead of print - 23 Dec 2019

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