Issue 35, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
09 Apr 2012
Accepted
11 Jul 2012
First published
13 Jul 2012

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

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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