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A vinylogous Michael reaction of 2-furanone dimers with α,β-unsaturated nitroolefins for constructing chiral γ,γ-disubstituted butenolides

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Abstract

An efficient bifunctional thiourea-catalyzed asymmetric vinylogous Michael addition of 2-furanone dimers to α,β-unsaturated nitroolefins has been developed to afford functional chiral γ,γ-disubstituted butenolides in good yields (up to 95%) with good to excellent stereoselectivity (up to >20 : 1 dr, 99% ee). DFT calculations were carried out to explain the high stereoselectivity.

Graphical abstract: A vinylogous Michael reaction of 2-furanone dimers with α,β-unsaturated nitroolefins for constructing chiral γ,γ-disubstituted butenolides

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Article information


Submitted
27 Mar 2020
Accepted
30 Apr 2020
First published
09 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

A vinylogous Michael reaction of 2-furanone dimers with α,β-unsaturated nitroolefins for constructing chiral γ,γ-disubstituted butenolides

Z. Bai, C. Zhang, Y. Chen, A. Liu, X. Wang, C. Yan, X. Liu, X. Zhang, Y. Li, Y. Yuan, Z. Ge, J. Pang, Y. Chai, X. Wang and R. Li, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00376J

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