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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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Indexed by:Journal Papers

First Author:Cheng, Ping

Correspondence Author:Du, X (reprint author), Dalian Univ Technol, Dept Chem, 2 Linggong Rd, Dalian 116024, Peoples R China.; Liu, Y; Li, C (reprint author), Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, 457 Zhongshan Rd, Dalian 116023, Peoples R China.

Co-author:Guo, Wengang,Chen, Ping,Liu, Yan,Du, Xin,Li, Can

Date of Publication:2016-02-25

Journal:CHEMICAL COMMUNICATIONS

Included Journals:SCIE、PubMed

Volume:52

Issue:16

Page Number:3418-3421

ISSN No.: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.

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