Issue 5, 2011
From the journal:

Organic & Biomolecular Chemistry

Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines†

Alok Singh,a   Bongchan Kim,b   Won Koo Lee*b  and  Hyun-Joon Ha*a  

* Corresponding authors

a Department of Chemistry and Protein Research Centre for Bio-Industry, Hankuk University of Foreign Studies, Yongin, Korea
E-mail: hjha@hufs.ac.kr
Fax: +82-31-3304566
Tel: +82-31-3304369

b Department of Chemistry, Sogang University, Seoul 121-742, Korea
E-mail: wonkoo@sogang.ac.kr
Fax: +82-2-7010967
Tel: +82-2-7058449

Abstract

A general and facile synthesis of enantiopure 1-deoxyazasugars was achieved from stereoselective dihydroxylation of a common synthetic intermediate, piperidine ring fused oxazolidin-2-one, originating from a commercially available starting substrate, chiral aziridine-2-carboxylate, in high yields.

Graphical abstract: Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines

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Article information

DOI
https://doi.org/10.1039/C0OB00730G
Article type
Paper
Submitted
16 Sep 2010
Accepted
03 Nov 2010
First published
04 Nov 2010

Org. Biomol. Chem., 2011,9, 1372-1380

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Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines

A. Singh, B. Kim, W. K. Lee and H. Ha, Org. Biomol. Chem., 2011, 9, 1372 DOI: 10.1039/C0OB00730G

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