Issue 12, 2024

NHC-catalyzed stereoselective synthesis of spirooxindole lactones from in situ generated oxindole-embedded o-quinone methides and aldehydes

Abstract

A novel N-heterocyclic carbene-catalyzed asymmetric [4 + 2] annulation of in situ generated oxindole-embedded o-quinone methides with aldehydes has been developed for synthesis of complicated spirooxindoles. The methodology provides facile, straightforward access to various enantioenriched spirooxindole lactones bearing a chiral quaternary carbon center in high yield (up to 98%) with diastereoselectivity (up to >20 : 1 dr) and excellent enantioselectivity (up to >99% ee).

Graphical abstract: NHC-catalyzed stereoselective synthesis of spirooxindole lactones from in situ generated oxindole-embedded o-quinone methides and aldehydes

Supplementary files

Article information

Article type
Research Article
Submitted
23 Feb 2024
Accepted
20 Apr 2024
First published
22 Apr 2024

Org. Chem. Front., 2024,11, 3326-3332

NHC-catalyzed stereoselective synthesis of spirooxindole lactones from in situ generated oxindole-embedded o-quinone methides and aldehydes

Z. Cao, F. Hu, Y. Chu, J. Pei and X. Hui, Org. Chem. Front., 2024, 11, 3326 DOI: 10.1039/D4QO00347K

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