Issue 15, 2015

Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3′-disubstituted oxindoles with chiral squaramides

Abstract

A highly enantioselective Michael addition of 3-monosubstituted oxindoles to α,β-unsaturated acyl phosphonates with chiral squaramides as catalysts is investigated for the first time. A wide range of 3,3′-disubstituted oxindole adducts bearing adjacent quaternary and tertiary stereogenic centres could be smoothly obtained in good yields (up to 98%), diastereo- (up to >99 : 1 dr) and enantioselectivities (up to 98% ee) with the developed protocols.

Graphical abstract: Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3′-disubstituted oxindoles with chiral squaramides

Supplementary files

Article information

Article type
Communication
Submitted
14 Feb 2015
Accepted
04 Mar 2015
First published
04 Mar 2015

Org. Biomol. Chem., 2015,13, 4413-4417

Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3′-disubstituted oxindoles with chiral squaramides

L. Chen, Y. You, M. Zhang, J. Zhao, J. Zuo, X. Zhang, W. Yuan and X. Xu, Org. Biomol. Chem., 2015, 13, 4413 DOI: 10.1039/C5OB00317B

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