Issue 19, 2021

Catalytic asymmetric umpolung reactions of imines via 2-azaallyl anion intermediates

Abstract

The imine umpolung is a relatively new and interesting strategy, especially in catalytic asymmetric synthesis. A significant development in organo- and transition metal-catalyzed umpolung of imines took place only in the recently concluded decade. A majority of the reports on the asymmetric umpolung of imines involve the initial generation of 2-azaallyl anion intermediates with the chiral catalysts, which serve as a significant driving force for the umpolung addition/substitution reactions. A variety of organocatalysts such as bifunctional cinchona alkaloids including squaramides and thioureas, chiral BINOL derived phosphoric acids, phase transfer catalysts (PTCs), phosphines, and transition metal-complexes of iridium, copper and palladium have been employed to achieve the excellent level of asymmetric induction in such types of umpolung reactions. The asymmetric imine umpolung strategy has been applied successfully to synthesize synthetic amino-acid derivatives and other useful chiral amines, including drugs and potentially bioactive molecules. This review summarizes all the significant recent development in catalytic umpolung reactions of imines involving a 2-azaallyl anion intermediate.

Graphical abstract: Catalytic asymmetric umpolung reactions of imines via 2-azaallyl anion intermediates

Article information

Article type
Review Article
Submitted
03 mar 2021
Accepted
23 mar 2021
First published
23 mar 2021

Org. Biomol. Chem., 2021,19, 4193-4212

Catalytic asymmetric umpolung reactions of imines via 2-azaallyl anion intermediates

Y. Hussain and P. Chauhan, Org. Biomol. Chem., 2021, 19, 4193 DOI: 10.1039/D1OB00409C

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