Issue 24, 2010
From the journal:

Chemical Communications

Highly diastereo- and enantioselective Mannich reaction of lactones with N-Boc-aldimines catalyzed by bifunctional rosin-derived amine thiourea catalysts†‡

Xianxing Jiang,ab   Dan Fu,a   Gen Zhang,a   Yiming Cao,a   Luping Liu,a   Jingjing Songa  and  Rui Wang*ab  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, China
E-mail: wangrui@lzu.edu.cn
Fax: (+86)-931-8911255

b Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong
E-mail: bcrwang@polyu.edu.h

Abstract

A highly efficient diastereo- and enantioselective Mannich reaction of lactones with a variety of N-Boc-aldimines by using bifunctional rosin-derived amine thiourea catalysts was investigated for the first time, in general, affording the adducts bearing quaternary stereogenic centers with high levels of enantio- and diastereoselectivity (up to 99% ee, and >20 : 1 dr).

Graphical abstract: Highly diastereo- and enantioselective Mannich reaction of lactones with N-Boc-aldimines catalyzed by bifunctional rosin-derived amine thiourea catalysts

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C000621A
Article type
Communication
Submitted
11 Jan 2010
Accepted
29 Apr 2010
First published
17 May 2010

Chem. Commun., 2010,46, 4294-4296

Permissions

Request permissions

Highly diastereo- and enantioselective Mannich reaction of lactones with N-Boc-aldimines catalyzed by bifunctional rosin-derived amine thiourea catalysts

X. Jiang, D. Fu, G. Zhang, Y. Cao, L. Liu, J. Song and R. Wang, Chem. Commun., 2010, 46, 4294 DOI: 10.1039/C000621A

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