Issue 21, 2011
From the journal:

Organic & Biomolecular Chemistry

One pot synthesis of amino acid derived chiral disubstituted morpholines and 1,4-oxazepanes via tandem aziridine/epoxide ring opening sequences†

Krishnananda Samantaa  and  Gautam Panda*a  

* Corresponding authors

a Medicinal and Process Chemistry Division, CSIR, Central Drug Research Institute, Lucknow, UP, India
E-mail: gautam.panda@gmail.com, gautam_panda@cdri.res.in
Fax: +91-522-2623405
Tel: +91-522-2612411-18, Ext. 4385, 4603

Abstract

A new one-pot synthetic strategy is described for the synthesis of enantiomerically pure cis-3,5-disubstituted morpholines and 3,6-disubstituted 1,4-oxazepanes via tandem aziridine/epoxide ring opening sequences. This new strategy describes how epoxy alcohols could act as both a nucleophile and an electrophile in a tandem fashion and undergo intermolecular regioselective ring opening of chiral aziridines for the first time.

Graphical abstract: One pot synthesis of amino acid derived chiral disubstituted morpholines and 1,4-oxazepanes via tandem aziridine/epoxide ring opening sequences

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Article information

DOI
https://doi.org/10.1039/C1OB05462G
Article type
Paper
Submitted
23 Mar 2011
Accepted
22 Jun 2011
First published
22 Jun 2011

Org. Biomol. Chem., 2011,9, 7365-7371

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One pot synthesis of amino acid derived chiral disubstituted morpholines and 1,4-oxazepanes via tandem aziridine/epoxide ring opening sequences

K. Samanta and G. Panda, Org. Biomol. Chem., 2011, 9, 7365 DOI: 10.1039/C1OB05462G

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