Issue 2, 2022

Brønsted acid-catalyzed enantioselective addition of 1,3-diones to in situ generated N-acyl ketimines

Abstract

A Brønsted acid-catalyzed asymmetric Mannich-type addition of 1,3-diones to cyclic N-acyl ketimines is reported for the synthesis of enantioenriched isoindolinones. Various dicarbonyl-substituted isoindolinones bearing a quaternary carbon stereocenter were synthesized with excellent yields (up to 98%) and moderate to high enantioselectivities (up to 95% ee), and most of them possess a fluorine atom at the reactive center. Furthermore, the synthetic utility of the protocol has been demonstrated by the debenzoylation of the product.

Graphical abstract: Brønsted acid-catalyzed enantioselective addition of 1,3-diones to in situ generated N-acyl ketimines

Supplementary files

Article information

Article type
Paper
Submitted
03 Nov 2021
Accepted
03 Dec 2021
First published
03 Dec 2021

Org. Biomol. Chem., 2022,20, 410-414

Brønsted acid-catalyzed enantioselective addition of 1,3-diones to in situ generated N-acyl ketimines

M. M. Sadhu, S. K. Ray, R. A. Unhale and V. K. Singh, Org. Biomol. Chem., 2022, 20, 410 DOI: 10.1039/D1OB02162A

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