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Stereoselective Synthesis of Chiral Oxepanes and Pyrans through Intramolecular Nitrone Cycloaddition in Organized Aqueous Media

IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata

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Title Stereoselective Synthesis of Chiral Oxepanes and Pyrans through Intramolecular Nitrone Cycloaddition in Organized Aqueous Media
 
Creator Chatterjee, Amrita
Bhattacharya, Pranab K
 
Subject Chemistry
 
Description A highly stereoselective surfactant-catalyzed intramolecular nitrone (formed by dehydration in water) cycloaddition in aqueous media leading to exclusive formation of a single isomer is reported. Either oxepane or pyran is formed from 3-O-allyl furanoside derivatives, which constitute the framework of a large number of biologically active compounds. Therefore, the environmentally friendly, efficient, and highly stereoselective syntheses of these chiral intermediates are still a meaningful pursuit.
 
Date 2006
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/398/1/JOURNAL_OF_ORGANIC_CHEMISTRY%2C__71(_1)%2C_345%2D348_[143].pdf
Chatterjee, Amrita and Bhattacharya, Pranab K (2006) Stereoselective Synthesis of Chiral Oxepanes and Pyrans through Intramolecular Nitrone Cycloaddition in Organized Aqueous Media. The Journal of Organic Chemistry, 71. pp. 345-348.
 
Relation http://dx.doi.org/10.1021/jo051414j CCC: $33.50
http://www.eprints.iicb.res.in/398/