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Organocatalytic asymmetric tandem α-functionalization/1,3-proton shift reaction of benzylidene succinimides with β-trifluoromethyl enones

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Abstract

A bifunctional thiourea-catalyzed asymmetric tandem α-functionalization/1,3-proton shift reaction of benzylidene succinimides with β-trifluoromethyl enones has been developed. A series of F3C-containing chiral Rauhut–Currier type products were obtained in moderate to high yields (up to 98%) with excellent enantioselectivities (up to >99% ee). This represents the first example of benzylidene succinimides undergoing tandem α-functionalization/1,3-proton shift in catalytic enantioselective transformation.

Graphical abstract: Organocatalytic asymmetric tandem α-functionalization/1,3-proton shift reaction of benzylidene succinimides with β-trifluoromethyl enones

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Article information


Submitted
11 Aug 2020
Accepted
02 Oct 2020
First published
02 Oct 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Organocatalytic asymmetric tandem α-functionalization/1,3-proton shift reaction of benzylidene succinimides with β-trifluoromethyl enones

X. Zhang, Y. You, Z. Wang, J. Zhao and W. Yuan, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC05474G

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