Release Time:2019-03-09  Hits:

Indexed by: Journal Papers

Date of Publication: 2016-02-25

Journal: CHEMICAL COMMUNICATIONS

Included Journals: PubMed、SCIE

Volume: 52

Issue: 16

Page Number: 3418-3421

ISSN: 1359-7345

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.