Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives

Bo Zhu; Wen Zhang; Richmond Lee; Zhiqiang Han; Wenguo Yang; Davin Tan; Kuo-Wei Huang; Zhiyong Jiang

doi:10.1002/anie.201302274

Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives

Bo Zhu, Wen Zhang, Richmond Lee, Zhiqiang Han, Wenguo Yang, Davin Tan, Kuo-Wei Huang, Zhiyong Jiang

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

165 Scopus citations

Abstract

6 in 1: The highly enantioselective title reaction is mediated by a bifunctional catalyst and leads to E-configured vinylogous aldol products (see scheme). These products are used as common intermediates in the synthesis of six biologically active 3-hydroxy-2-oxindole derivatives (e.g., CPC-1). Computational studies indicated that the observed stereoselectivity is a result of favorable secondary π-π* and H-bonding interactions in the transition state. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	6666-6670
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	26
DOIs	https://doi.org/10.1002/anie.201302274
State	Published - May 3 2013

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.201302274

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title = "Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives",

abstract = "6 in 1: The highly enantioselective title reaction is mediated by a bifunctional catalyst and leads to E-configured vinylogous aldol products (see scheme). These products are used as common intermediates in the synthesis of six biologically active 3-hydroxy-2-oxindole derivatives (e.g., CPC-1). Computational studies indicated that the observed stereoselectivity is a result of favorable secondary π-π* and H-bonding interactions in the transition state. Copyright {\textcopyright} 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

author = "Bo Zhu and Wen Zhang and Richmond Lee and Zhiqiang Han and Wenguo Yang and Davin Tan and Kuo-Wei Huang and Zhiyong Jiang",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the NSFC (21072044) and the Program for New Century Excellent Talents in University of the Ministry of Education (NCET-11-0938) to Z.J. and by KAUST to K.-W.H.",

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journal = "Angewandte Chemie - International Edition",

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T1 - Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives

AU - Zhu, Bo

AU - Zhang, Wen

AU - Lee, Richmond

AU - Han, Zhiqiang

AU - Yang, Wenguo

AU - Tan, Davin

AU - Huang, Kuo-Wei

AU - Jiang, Zhiyong

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the NSFC (21072044) and the Program for New Century Excellent Talents in University of the Ministry of Education (NCET-11-0938) to Z.J. and by KAUST to K.-W.H.

PY - 2013/5/3

Y1 - 2013/5/3

N2 - 6 in 1: The highly enantioselective title reaction is mediated by a bifunctional catalyst and leads to E-configured vinylogous aldol products (see scheme). These products are used as common intermediates in the synthesis of six biologically active 3-hydroxy-2-oxindole derivatives (e.g., CPC-1). Computational studies indicated that the observed stereoselectivity is a result of favorable secondary π-π* and H-bonding interactions in the transition state. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - 6 in 1: The highly enantioselective title reaction is mediated by a bifunctional catalyst and leads to E-configured vinylogous aldol products (see scheme). These products are used as common intermediates in the synthesis of six biologically active 3-hydroxy-2-oxindole derivatives (e.g., CPC-1). Computational studies indicated that the observed stereoselectivity is a result of favorable secondary π-π* and H-bonding interactions in the transition state. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

UR - http://hdl.handle.net/10754/562755

UR - http://doi.wiley.com/10.1002/anie.201302274

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U2 - 10.1002/anie.201302274

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SP - 6666

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 26

ER -

Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives

Abstract

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CCDC 881668: Experimental Crystal Structure Determination : 7-Chloro-3-hydroxy-3-(4-(3-methoxyphenyl)-4-oxobut-2-en-1-yl)-1,3-dihydro-2H-indol-2-one

Cite this

Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives

Abstract

ASJC Scopus subject areas

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CCDC 881668: Experimental Crystal Structure Determination : 7-Chloro-3-hydroxy-3-(4-(3-methoxyphenyl)-4-oxobut-2-en-1-yl)-1,3-dihydro-2H-indol-2-one

Cite this