Unanticipated silyl transfer in enantioselective α,β-unsaturated acyl ammonium catalysis using silyl nitronates
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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.
Matviitsuk , A , Greenhalgh , M D , Taylor , J E , Nguyen , X B , Cordes , D B , Slawin , A M Z , Lupton , D W & Smith , A D 2019 , ' Unanticipated silyl transfer in enantioselective α,β-unsaturated acyl ammonium catalysis using silyl nitronates ' , Organic Letters , vol. Article ASAP . https://doi.org/10.1021/acs.orglett.9b04404
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DescriptionWe thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013), ERC Grant Agreement 279850 (A.D.S.), the EPSRC (EP/J018139/1, A.M.), and the Royal Society of Chemistry (Researcher Mobility Grant). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. D.W.L. thanks the Australian Research Council for a Discovery Award (DP170103567). We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.
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