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

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Title Stereoselective Synthesis of cis-2,6-Disubstituted Morpholines and 1,4-Oxathianes by Intramolecular Reductive Etherification of 1,5-Diketones
 
Creator GHARPURE, SJ
ANURADHA, D
PRASAD, JVK
RAO, PS
 
Subject 2,6-DISUBSTITUTED MORPHOLINES
GLYCOSYL DONORS
CYCLIC ETHERS
ENANTIOSELECTIVE SYNTHESIS
PSEUDOAXIAL CONFORMERS
FACILE PREPARATION
OXOCARBENIUM IONS
SULFUR-DIOXIDE
DERIVATIVES
OXATHIANE
Morpholines
1
4-Oxathianes
Diketones
Lewis acids
Reductive etherification
Natural products
 
Description 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 products (+/-)-chelonin A and formal total synthesis of (+/-)-chelonin C.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2016-01-14T10:37:51Z
2016-01-14T10:37:51Z
2015
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(1)86-90
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201403294
http://dspace.library.iitb.ac.in/jspui/handle/100/17378
 
Language en