Issue 37, 2024

A quinine-squaramide catalyzed enantioselective vinylogous Mannich reaction between benzothiazolimines and γ-butenolides for efficient preparation of chiral N-benzothiazole butyrolactones

Abstract

A highly effective and enantioselective vinylogous Mannich reaction between benzothiazolimines and γ-butenolides catalyzed by a quinine based squaramide has been disclosed. A series of chiral benzothiazole amines containing a γ,γ-disubstituted butanolide scaffold bearing an adjacent chiral stereocenter have been successfully obtained in good to excellent yields (up to 91%) with excellent enantioselectivities (up to >99% ee) and diastereoselectivities (>20 : 1 dr) with broad substrate generality under mild conditions. The new scaffold integrated with both chiral benzothiazolimine and γ-butenolide moieties may provide a possibility for the development of new pharmaceutical entities.

Graphical abstract: A quinine-squaramide catalyzed enantioselective vinylogous Mannich reaction between benzothiazolimines and γ-butenolides for efficient preparation of chiral N-benzothiazole butyrolactones

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Article information

Article type
Communication
Submitted
16 Jul 2024
Accepted
21 Aug 2024
First published
22 Aug 2024

Org. Biomol. Chem., 2024,22, 7612-7617

A quinine-squaramide catalyzed enantioselective vinylogous Mannich reaction between benzothiazolimines and γ-butenolides for efficient preparation of chiral N-benzothiazole butyrolactones

J. Yu, Q. Zhang, G. Cheng, C. Tang, Z. Yang, W. Li and L. Wang, Org. Biomol. Chem., 2024, 22, 7612 DOI: 10.1039/D4OB01175A

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