Issue 21, 2011

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 Mar 2011
Accepted
22 Jun 2011
First published
22 Jun 2011

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

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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