Issue 40, 2014
From the journal:

Organic & Biomolecular Chemistry

Enantioselective aza-Morita–Baylis–Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles†

Xuan Zhao,a   Tian-Ze Li,a   Jing-Ying Qian,a   Feng Sha*a  and  Xin-Yan Wu*a  

* Corresponding authors

a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China
E-mail: xinyanwu@ecust.edu.cn
Tel: +86-21-64252011

Abstract

The first enantioselective aza-Morita–Baylis–Hillman reaction of acrylates with ketimines derived from isatins has been developed. With 2 mol% of chiral bifunctional phosphine-squaramide 4e, optically active 3-substituted-3-amino-2-oxindoles were obtained in excellent yields with up to 91% ee.

Graphical abstract: Enantioselective aza-Morita–Baylis–Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles

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Article information

DOI
https://doi.org/10.1039/C4OB01358A
Article type
Paper
Submitted
30 Jun 2014
Accepted
15 Aug 2014
First published
15 Aug 2014

Org. Biomol. Chem., 2014,12, 8072-8078

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Enantioselective aza-Morita–Baylis–Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles

X. Zhao, T. Li, J. Qian, F. Sha and X. Wu, Org. Biomol. Chem., 2014, 12, 8072 DOI: 10.1039/C4OB01358A

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