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Issue 16, 2016
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The enantioselective construction of chiral spirooxindole-based 4-thiazolidinone via asymmetric catalytic formal [3+2] annulation using a bifunctional catalyst

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Abstract

4-Thiazolidinone is regarded as a privileged structural unit in bioactive compounds. However, there is still no example of a catalytic method for the synthesis of chiral 4-thiazolidinone until now. We reported herein a facile and efficient method for the construction of chiral spirooxindole-based 4-thiazolidinone. This methodology is based on the asymmetric formal [3+2] annulation of 1,4-dithiane-2,5-diol to ketimines which is followed by simple oxidation, featuring a broad substrate scope with high enantioselectivity (up to 98% ee). The method has been successfully applied to the synthesis of a novel class of mycobacterium tuberculosis inhibitor-spirooxindole based 4-thiazolidinone.

Graphical abstract: The enantioselective construction of chiral spirooxindole-based 4-thiazolidinone via asymmetric catalytic formal [3+2] annulation using a bifunctional catalyst

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Publication details

The article was received on 15 Dec 2015, accepted on 26 Jan 2016 and first published on 02 Feb 2016


Article type: Communication
DOI: 10.1039/C5CC10292H
Citation: Chem. Commun., 2016,52, 3418-3421
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    The enantioselective construction of chiral spirooxindole-based 4-thiazolidinone via asymmetric catalytic formal [3+2] annulation using a bifunctional catalyst

    P. Cheng, W. Guo, P. Chen, Y. Liu, X. Du and C. Li, Chem. Commun., 2016, 52, 3418
    DOI: 10.1039/C5CC10292H

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