Issue 11, 2011
From the journal:

Chemical Communications

A facile direct anti-selective catalytic asymmetric Mannich reaction of aldehydes with preformed N-Boc and N-Cbz imines†

Yong-Ming Chuan,ab   Gui-Hua Chen,ab   Jiu-Zhi Gao,a   Hui Zhanga  and  Yun-Gui Peng*a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Southwest University, Chongqing, P.R. China
E-mail: pyg@swu.edu.cn
Fax: +86 23-6825-3157

b Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences (CAS), Chengdu, P.R. China

Abstract

Anti-selective Mannich reactions of N-Boc and N-Cbz protected imines with unmodified aldehydes proceeded smoothly under the catalysis of a secondary amine–thiourea catalyst, which led to high yields (70%–95%) and excellent enantioselectivity (up to 96 ∶ 4 dr and >99% ee) under conventional organic synthetic operations.

Graphical abstract: A facile direct anti-selective catalytic asymmetric Mannich reaction of aldehydes with preformed N-Boc and N-Cbz imines

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Article information

DOI
https://doi.org/10.1039/C0CC05249C
Article type
Communication
Submitted
29 Nov 2010
Accepted
12 Jan 2011
First published
31 Jan 2011

Chem. Commun., 2011,47, 3260-3262

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A facile direct anti-selective catalytic asymmetric Mannich reaction of aldehydes with preformed N-Boc and N-Cbz imines

Y. Chuan, G. Chen, J. Gao, H. Zhang and Y. Peng, Chem. Commun., 2011, 47, 3260 DOI: 10.1039/C0CC05249C

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