Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions

Wen Zhang; Davin Tan; Richmond Lee; Guanghu Tong; Wenchao Chen; Baojian Qi; Kuo-Wei Huang; Choonhong Tan; Zhiyong Jiang

doi:10.1002/anie.201205872

Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions

Wen Zhang, Davin Tan, Richmond Lee, Guanghu Tong, Wenchao Chen, Baojian Qi, Kuo-Wei Huang, Choonhong Tan, Zhiyong Jiang

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

122 Scopus citations

Abstract

The strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	10069-10073
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	51
Issue number	40
DOIs	https://doi.org/10.1002/anie.201205872
State	Published - Sep 5 2012

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was supported by the NSFC (21072044) and the Excellent Youth Foundation of Henan Scientific Committee (114100510003) to Z.J., and by KAUST to K.-W.H.

ASJC Scopus subject areas

Chemistry(all)
Catalysis

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10.1002/anie.201205872

Cite this

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title = "Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions",

abstract = "The strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright {\textcopyright} 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

author = "Wen Zhang and Davin Tan and Richmond Lee and Guanghu Tong and Wenchao Chen and Baojian Qi and Kuo-Wei Huang and Choonhong Tan and Zhiyong Jiang",

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T1 - Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions

AU - Zhang, Wen

AU - Tan, Davin

AU - Lee, Richmond

AU - Tong, Guanghu

AU - Chen, Wenchao

AU - Qi, Baojian

AU - Huang, Kuo-Wei

AU - Tan, Choonhong

AU - Jiang, Zhiyong

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the NSFC (21072044) and the Excellent Youth Foundation of Henan Scientific Committee (114100510003) to Z.J., and by KAUST to K.-W.H.

PY - 2012/9/5

Y1 - 2012/9/5

N2 - The strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - The strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions

Abstract

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CCDC 887648: Experimental Crystal Structure Determination : Methyl 3-(2-(4-chlorophenyl)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)propanoate

CCDC 887626: Experimental Crystal Structure Determination : 3-(4,4,4-Trifluoro-3-(2-methyl-5-oxo-2,5-dihydrofuran-2-yl)butanoyl)-1,3-oxazolidin-2-one

CCDC 886753: Experimental Crystal Structure Determination : 2-(2-(4-Chlorophenyl)-5-oxo-2,5-dihydrofuran-2-yl)-1-(2-oxo-1,3-oxazolidin-3-yl)-4-phenylbutane-1,4-dione

Cite this

Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

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Datasets

CCDC 887648: Experimental Crystal Structure Determination : Methyl 3-(2-(4-chlorophenyl)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)propanoate

CCDC 887626: Experimental Crystal Structure Determination : 3-(4,4,4-Trifluoro-3-(2-methyl-5-oxo-2,5-dihydrofuran-2-yl)butanoyl)-1,3-oxazolidin-2-one

CCDC 886753: Experimental Crystal Structure Determination : 2-(2-(4-Chlorophenyl)-5-oxo-2,5-dihydrofuran-2-yl)-1-(2-oxo-1,3-oxazolidin-3-yl)-4-phenylbutane-1,4-dione

Cite this