Stereoselective Synthesis ofcis-2,6-Disubstituted Morpholines and 1,4-Oxathianes by Intramolecular Reductive Etherification of 1,5-Diketones

Gharpure, Santosh J. ; Anuradha, Dandela ; Prasad, Jonnalagadda V. K. ; Srinivasa Rao, Pidugu (2014) Stereoselective Synthesis ofcis-2,6-Disubstituted Morpholines and 1,4-Oxathianes by Intramolecular Reductive Etherification of 1,5-Diketones European Journal of Organic Chemistry, 2015 (1). pp. 86-90. ISSN 1434-193X

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Official URL: http://doi.org/10.1002/ejoc.201403294

Related URL: http://dx.doi.org/10.1002/ejoc.201403294

Abstract

A simple and efficient, Lewis acid catalysed reductive etherification strategy for the stereoselective synthesis of cis-2,6-disubstituted morpholines and 1,4-oxathianes starting from readily available 1,5-diketones has been developed. The strategy is used in the total synthesis of morpholine-based natural product (±)-chelonin A and a formal total synthesis of (±)-chelonin C.

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Deposited On:09 Dec 2022 06:28
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