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

doi:10.1021/acs.orglett.9b04404

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

School of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

17 Citations (Scopus)

Abstract

The use of silyl nitronates is reported for the isothiourea-catalyzed synthesis of Î³-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 language	English
Pages (from-to)	335-339
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.9b04404
Publication status	Published - 3 Jan 2020

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10.1021/acs.orglett.9b04404

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

abstract = "The use of silyl nitronates is reported for the isothiourea-catalyzed synthesis of {\^I}³-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.",

author = "Anastassia Matviitsuk and Greenhalgh, {Mark D.} and Taylor, {James E.} and Nguyen, {Xuan B.} and Cordes, {David B.} and Slawin, {Alexandra M.Z.} and Lupton, {David W.} and Smith, {Andrew D.}",

year = "2020",

month = jan,

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doi = "10.1021/acs.orglett.9b04404",

language = "English",

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journal = "Organic Letters",

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T1 - Unanticipated Silyl Transfer in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis Using Silyl Nitronates

AU - Matviitsuk, Anastassia

AU - Greenhalgh, Mark D.

AU - Taylor, James E.

AU - Nguyen, Xuan B.

AU - Cordes, David B.

AU - Slawin, Alexandra M.Z.

AU - Lupton, David W.

AU - Smith, Andrew D.

PY - 2020/1/3

Y1 - 2020/1/3

N2 - The use of silyl nitronates is reported for the isothiourea-catalyzed synthesis of Î³-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.

AB - The use of silyl nitronates is reported for the isothiourea-catalyzed synthesis of Î³-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.

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U2 - 10.1021/acs.orglett.9b04404

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JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

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

Abstract

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C=C insertion, C-H bond functionalisation, challenges to organocatalysis.

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

Abstract

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Projects

C=C insertion, C-H bond functionalisation, challenges to organocatalysis.

Cite this