Issue 1, 2022

Efficient enantioselective synthesis of CF2H-containing dispiro[benzo[b]thiophene-oxindole-pyrrolidine]s via organocatalytic cycloaddition

Abstract

An efficient and practical organocatalytic asymmetric [3 + 2] cycloaddition of difluoromethylated ketoimines and methyleneindolinones catalyzed by a quinine-derived squaramide has been disclosed. Under mild conditions, a broad range of CF2H-containing dispiro[benzo[b]thiophene-oxindole-pyrrolidine]s bearing four adjacent chiral centers including two vicinal spiro quaternary stereocenters were obtained in high yields (up to 99% yield) with excellent diastereoselectivities (>20 : 1 dr, in all cases) and enantioselectivities (up to 99% ee).

Graphical abstract: Efficient enantioselective synthesis of CF2H-containing dispiro[benzo[b]thiophene-oxindole-pyrrolidine]s via organocatalytic cycloaddition

Supplementary files

Article information

Article type
Research Article
Submitted
16 Sep 2021
Accepted
23 Nov 2021
First published
24 Nov 2021

Org. Chem. Front., 2022,9, 210-215

Efficient enantioselective synthesis of CF2H-containing dispiro[benzo[b]thiophene-oxindole-pyrrolidine]s via organocatalytic cycloaddition

Y. Deng, Y. Li, Y. Wang, S. Sun, S. Ma, P. Jia, W. Li, K. Wang and W. Yan, Org. Chem. Front., 2022, 9, 210 DOI: 10.1039/D1QO01392K

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