Thiosquaramide-catalysed asymmetric double Michael addition of 2-(3H)-furanones to nitroolefines

Mengchen Yang; Chen Chen; Xing Yi; Yuan Li; Xiaoqin Wu; Qingshan Li; Shurong Ban

doi:10.1039/C9OB00330D

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Thiosquaramide-catalysed asymmetric double Michael addition of 2-(3H)-furanones to nitroolefines†

Mengchen Yang,‡^a Chen Chen,‡^a Xing Yi,^a Yuan Li,^a Xiaoqin Wu,^b Qingshan Li*^ac and Shurong Ban

*^ac

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* Corresponding authors

^a School of Pharmacy, Shanxi Medical University, Taiyuan, Shanxi, China
E-mail: qingshanl@yahoo.com, shurongban@sxmu.edu.cn

^b Scientific Instrument Center, Shanxi University, Taiyuan, Shanxi, China

^c Shanxi Key laboratory of Chronic Inflammatory Targeted Drugs, Shanxi University of Traditional Chinese Medicine, Jinzhong, Shanxi, China

Abstract

New chiral thiosquaramides and their applications in catalytic asymmetric double addition of 5-methyl-2(3H)-furanones to nitroolefins were described. Enantiomerically enriched 2,4,4-trisubstituted butenolides bearing a quaternary stereogenic center could be smoothly constructed with high diastereoselectivities (up to >99 : 1 dr) and excellent enantioselectivities (up to 95% ee) under mild conditions.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/C9OB00330D
Article type: Communication
Submitted: 10 Feb 2019
Accepted: 15 Feb 2019
First published: 16 Feb 2019

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Org. Biomol. Chem., 2019,17, 2883-2886

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Thiosquaramide-catalysed asymmetric double Michael addition of 2-(3H)-furanones to nitroolefines

M. Yang, C. Chen, X. Yi, Y. Li, X. Wu, Q. Li and S. Ban, Org. Biomol. Chem., 2019, 17, 2883 DOI: 10.1039/C9OB00330D

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Organic & Biomolecular Chemistry

Thiosquaramide-catalysed asymmetric double Michael addition of 2-(3H)-furanones to nitroolefines†

Abstract

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Thiosquaramide-catalysed asymmetric double Michael addition of 2-(3H)-furanones to nitroolefines

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