Issue 20, 2015
From the journal:

Organic & Biomolecular Chemistry

Maleimide as an efficient nucleophilic partner in the aza-Morita–Baylis–Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles†

Akshay Kumar,a   Vivek Sharma,a   Jasneet Kaur,a   Naveen Kumara  and  Swapandeep Singh Chimni*a  

* Corresponding authors

a Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, India
E-mail: sschimni@yahoo.com, sschimni.chem@gndu.ac.in
Fax: (+)91-183-2258820

Abstract

A highly enantioselective Morita–Baylis–Hillman reaction of maleimides with isatin derived ketimines has been developed to obtain enantiomerically enriched 3-substituted-3-aminooxindoles using β-isocupreidine as an organocatalyst. Maleimide acting as a nucleophile provides products with up to 99% ee.

Graphical abstract: Maleimide as an efficient nucleophilic partner in the aza-Morita–Baylis–Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles

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Article information

DOI
https://doi.org/10.1039/C5OB00182J
Article type
Paper
Submitted
29 Jan 2015
Accepted
24 Feb 2015
First published
24 Feb 2015

Org. Biomol. Chem., 2015,13, 5629-5635

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Maleimide as an efficient nucleophilic partner in the aza-Morita–Baylis–Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles

A. Kumar, V. Sharma, J. Kaur, N. Kumar and S. S. Chimni, Org. Biomol. Chem., 2015, 13, 5629 DOI: 10.1039/C5OB00182J

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