Issue 87, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
11 Aug 2020
Accepted
02 Oct 2020
First published
02 Oct 2020

Chem. Commun., 2020,56, 13449-13452

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, 56, 13449 DOI: 10.1039/D0CC05474G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements