Issue 35, 2012
From the journal:

Organic & Biomolecular Chemistry

Chiral phosphine-catalyzed asymmetric allylic alkylation of 3-substituted benzofuran-2(3H)-ones or oxindoles with Morita–Baylis–Hillman carbonates†

De Wang,a   Yuan-Liang Yang,a   Jia-Jun Jianga  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, China

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

Abstract

An efficient chiral phosphine-catalyzed asymmetric substitution reaction of MBH carbonates with 3-substituted benzofuran-2(3H)-ones or 3-substituted oxindoles has been described in this context, giving the corresponding allylic alkylation products bearing adjacent quaternary and tertiary stereogenic centers in high yields, moderate diastereoselectivities and high enantioselectivities under mild conditions.

Graphical abstract: Chiral phosphine-catalyzed asymmetric allylic alkylation of 3-substituted benzofuran-2(3H)-ones or oxindoles with Morita–Baylis–Hillman carbonates

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Article information

DOI
https://doi.org/10.1039/C2OB25694K
Article type
Paper
Submitted
09 Apr 2012
Accepted
11 Jul 2012
First published
13 Jul 2012

Org. Biomol. Chem., 2012,10, 7158-7166

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Chiral phosphine-catalyzed asymmetric allylic alkylation of 3-substituted benzofuran-2(3H)-ones or oxindoles with Morita–Baylis–Hillman carbonates

D. Wang, Y. Yang, J. Jiang and M. Shi, Org. Biomol. Chem., 2012, 10, 7158 DOI: 10.1039/C2OB25694K

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