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Issue 87, 2016
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Asymmetric Mannich reaction: highly enantioselective synthesis of 3-amino-oxindoles via chiral squaramide based H-bond donor catalysis

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Abstract

We describe here a simple and facile asymmetric Mannich reaction catalyzed by chiral Cinchona alkaloid based squaramide containing H-bond donor catalysts, wherein, the reaction of 1,3-diketones with isatin (N-Boc) ketimines led to the formation of 3-aminooxindole derivatives. These derivatives were obtained in high yields with excellent enantioselectivities under mild conditions using 3 mol% of the catalyst. This protocol provides valuable and easy access to chiral 3-substituted 3-aminooxindole derivatives.

Graphical abstract: Asymmetric Mannich reaction: highly enantioselective synthesis of 3-amino-oxindoles via chiral squaramide based H-bond donor catalysis

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Article information


Submitted
30 Jun 2016
Accepted
31 Aug 2016
First published
31 Aug 2016

RSC Adv., 2016,6, 84242-84247
Article type
Communication

Asymmetric Mannich reaction: highly enantioselective synthesis of 3-amino-oxindoles via chiral squaramide based H-bond donor catalysis

K. S. Rao, P. Ramesh, L. R. Chowhan and R. Trivedi, RSC Adv., 2016, 6, 84242
DOI: 10.1039/C6RA16877A

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