Issue 10, 2011
From the journal:

Chemical Science

Enantioselective Mannich reaction of a highly reactive Horner–Wadsworth–Emmons reagent with imines catalyzed by a bifunctional thiourea†

Depeng Zhao,a   Dongxu Yang,a   Yijie Wang,a   Yuan Wang,a   Linqing Wang,a   Lijuan Maoa  and  Rui Wang*ab  

* Corresponding authors

a Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Medicine, State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou, P. R. China
E-mail: wangrui@lzu.edu.cn
Tel: +86-9318912567

b State Key Laboratory of Chiroscience and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong

Abstract

N-acyl pyrrole phosphonates were identified as a class of highly reactive HWE reagents. The asymmetric addition of the present HWE reagents to N-carbamoyl imines generated in situ was achieved. The corresponding Mannich adducts can be further transformed to aza-MBH type products in good to excellent enantioselectivities.

Graphical abstract: Enantioselective Mannich reaction of a highly reactive Horner–Wadsworth–Emmons reagent with imines catalyzed by a bifunctional thiourea

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Article information

DOI
https://doi.org/10.1039/C1SC00351H
Article type
Edge Article
Submitted
09 Jun 2011
Accepted
23 Jun 2011
First published
13 Jul 2011

Chem. Sci., 2011,2, 1918-1921

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Enantioselective Mannich reaction of a highly reactive Horner–Wadsworth–Emmons reagent with imines catalyzed by a bifunctional thiourea

D. Zhao, D. Yang, Y. Wang, Y. Wang, L. Wang, L. Mao and R. Wang, Chem. Sci., 2011, 2, 1918 DOI: 10.1039/C1SC00351H

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