Issue 39, 2012
From the journal:

Organic & Biomolecular Chemistry

Enantioselective Michael addition of 3-aryloxindoles to a vinyl bisphosphonate ester catalyzed by a cinchona alkaloid derived thiourea catalyst†

Mei-Xin Zhao,*a   Tong-Lei Dai,a   Ran Liu,a   Deng-Ke Wei,a   Hao Zhou,a   Fei-Hu Jia  and  Min Shi*ab  

* Corresponding authors

a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, P.R. China
E-mail: mxzhao@ecust.edu.cn
Fax: +86-21-34201699

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P.R. China
E-mail: Mshi@mail.sioc.ac.cn
Fax: +86-21-64166128

Abstract

A highly enantioselective Michael addition of 3-aryloxindole to vinyl bisphosphonate ester catalyzed by a cinchonidine derived thiourea catalyst has been investigated. The corresponding adducts, containing a chiral quaternary carbon center and geminal bisphosphonate ester fragment at the 3-position of the oxindole, were obtained in moderate to good yields (65–92%) and moderate to good enantioselectivities (up to 92% ee).

Graphical abstract: Enantioselective Michael addition of 3-aryloxindoles to a vinyl bisphosphonate ester catalyzed by a cinchona alkaloid derived thiourea catalyst

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Article information

DOI
https://doi.org/10.1039/C2OB25966D
Article type
Paper
Submitted
19 May 2012
Accepted
02 Aug 2012
First published
02 Aug 2012

Org. Biomol. Chem., 2012,10, 7970-7979

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Enantioselective Michael addition of 3-aryloxindoles to a vinyl bisphosphonate ester catalyzed by a cinchona alkaloid derived thiourea catalyst

M. Zhao, T. Dai, R. Liu, D. Wei, H. Zhou, F. Ji and M. Shi, Org. Biomol. Chem., 2012, 10, 7970 DOI: 10.1039/C2OB25966D

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