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Tandem Nucleophilic Addition/Oxa-Michael Reaction for the Synthesis of cis-2,6-Disubstituted Tetrahydropyrans

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Title Tandem Nucleophilic Addition/Oxa-Michael Reaction for the Synthesis of cis-2,6-Disubstituted Tetrahydropyrans
 
Creator GHARPURE, SJ
PRASAD, JVK
BERA, K
 
Subject Oxygen heterocycles
Michael addition
Lewis acids
Domino reactions
Nucleophilic addition
STEREOSELECTIVE-SYNTHESIS
CONJUGATE ADDITION
VINYLOGOUS CARBONATES
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
NATURAL-PRODUCTS
CYCLIC ETHERS
CONSTRUCTION
CYCLIZATION
(-)-CENTROLOBINE
 
Description A Lewis acid catalyzed tandem nucleophilic addition/oxa-Michael reaction was developed for the synthesis of cis-2,6-disubstituted tetrahydropyran (THP) derivatives in good yields with excellent diastereoselectivities. The strategy was successfully used in the construction of THP derivatives with three stereocenters in a highly stereoselective fashion.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-12-28T11:20:24Z
2014-12-28T11:20:24Z
2014
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(17)3570-3574
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201402199
http://dspace.library.iitb.ac.in/jspui/handle/100/16343
 
Language English