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

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.

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    Abstract

    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.

    Item Type: Article
    URI: http://www.eprints.iicb.res.in/id/eprint/398
    Subjects: Chemistry
    Divisions: Indian Institute of Chemical Biology
    Depositing User: Ms Sutapa Ganguly
    Date Deposited: 31 Oct 2011 16:27
    Last Modified: 03 Feb 2012 11:33
    Official URL: http://dx.doi.org/10.1021/jo051414j CCC: $33.50
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