Issue 62, 2019
From the journal:

Chemical Communications

Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones†

Tiantian Cong,a   Huamin Wang,a   Xiuzheng Li,b   Hai-Hong Wu ORCID logo *a  and  Junliang Zhang ORCID logo *ac  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, P. R. China

b School of Pharmacy, Anhui Medical University, 81 N. Meishan Road, Hefei 230032, P. R. China

c Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, P. R. China
E-mail: junliangzhang@fudan.edu.cn

Abstract

A chiral phosphine-catalyzed tandem Michael addition of tryptamine-derived oxindoles to ynones has been developed, which provides facile access to a series of optically enriched spiro[pyrrolidine-3,3′-oxindole] compounds in good yields with good to excellent enantio- (up to 97% ee) and diastereoselectivities (up to 20 : 1 dr). Mechanistic studies indicate that this tandem reaction proceeds via an intermolecular aza-Michael/intramolecular Michael addition process.

Graphical abstract: Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C9CC04357H
Article type
Communication
Submitted
07 Jun 2019
Accepted
03 Jul 2019
First published
04 Jul 2019

Chem. Commun., 2019,55, 9176-9179

Permissions

Request permissions

Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones

T. Cong, H. Wang, X. Li, H. Wu and J. Zhang, Chem. Commun., 2019, 55, 9176 DOI: 10.1039/C9CC04357H

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