Issue 9, 2021

A new asymmetric activation strategy for hydrazones as acyl anion equivalents in the bimetallic catalyzed carbonyl-ene reaction

Abstract

A new asymmetric activation strategy for hydrazones as acyl anion equivalents is developed in the bimetallic catalyzed carbonyl-ene reaction of isatins and hydrazones. Under mild conditions, optically active functionalized 3-hydroxy-2-oxindoles were furnished in up to 98% yield with up to 97% enantioselectivity. In this process, formaldehyde tert-butylhydrazone which is seldom employed in asymmetric carbonyl-ene reactions accelerated by a metallic catalyst can be activated well by a Brønsted base. A possible catalytic cycle is proposed.

Graphical abstract: A new asymmetric activation strategy for hydrazones as acyl anion equivalents in the bimetallic catalyzed carbonyl-ene reaction

Supplementary files

Article information

Article type
Paper
Submitted
05 Jan 2021
Accepted
08 Feb 2021
First published
09 Feb 2021

Org. Biomol. Chem., 2021,19, 2055-2062

A new asymmetric activation strategy for hydrazones as acyl anion equivalents in the bimetallic catalyzed carbonyl-ene reaction

W. Hu, X. Song and M. Wang, Org. Biomol. Chem., 2021, 19, 2055 DOI: 10.1039/D1OB00017A

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