Issue 40, 2007
From the journal:

Chemical Communications

Highly diastereoselective and enantioselective direct organocatalytic anti-selective Mannich reactions employing N-tosylimines†

Lili Cheng,a   Xiao Han,a   Huiming Huang,a   Ming Wah Wonga  and  Yixin Lu*ab  

* Corresponding authors

a Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, Republic of Singapore
E-mail: chmlyx@nus.edu.sg
Fax: +65-6779-1691
Tel: +65-6516-1569

b The Medicinal Chemistry Program, Office of Life Sciences, National University of Singapore, Singapore

Abstract

Organocatalytic direct anti-selective Mannich reactions of O-TBS-hydroxyacetone with various N-tosylimines derived from aromatic aldehydes in the presence of L-threonine-derived catalyst afforded 1,2-amino alcohols in good yields and with enantioselectivities of 99% in almost all cases.

Graphical abstract: Highly diastereoselective and enantioselective direct organocatalytic anti-selective Mannich reactions employing N-tosylimines

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Article information

DOI
https://doi.org/10.1039/B706793C
Article type
Communication
Submitted
08 May 2007
Accepted
09 Jul 2007
First published
03 Aug 2007

Chem. Commun., 2007, 4143-4145

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Highly diastereoselective and enantioselective direct organocatalytic anti-selective Mannich reactions employing N-tosylimines

L. Cheng, X. Han, H. Huang, M. W. Wong and Y. Lu, Chem. Commun., 2007, 4143 DOI: 10.1039/B706793C

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