Issue 12, 2013

Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers

Abstract

The asymmetric catalytic aza-Morita–Baylis–Hillman (aza-MBH) reaction of isatin-derived ketimines with MVK has been established by using chiral amino and phosphino catalysts. The reaction resulted in biomedically important 3-substituted 3-amino-2-oxindoles in good yields (>80% for most cases) and with excellent enantioselectivity (90–99% ee). Twenty-eight cases assembled with chiral quaternary stereogenic centers have been examined under convenient systems.

Graphical abstract: Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers

Supplementary files

Article information

Article type
Communication
Submitted
23 Dec 2012
Accepted
31 Jan 2013
First published
01 Feb 2013

Org. Biomol. Chem., 2013,11, 1921-1924

Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers

F. Hu, Y. Wei, M. Shi, S. Pindi and G. Li, Org. Biomol. Chem., 2013, 11, 1921 DOI: 10.1039/C3OB27495K

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