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Regio- and Stereoselective Synthesis of Aziridino Epoxides from Cyclic Dienes

Sureshkumar, Devarajulu and Maity, Susama and Chandrasekaran, Srinivasan (2006) Regio- and Stereoselective Synthesis of Aziridino Epoxides from Cyclic Dienes. In: Journal Of Organic Chemistry, 71 (4). pp. 1653-1657.

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Official URL: http://pubs.acs.org/doi/pdf/10.1021/jo052357x


Two different routes for the regio- and stereoslective synthesis of aziridino epoxides from cyclic dienes have been explored. The first strategy involves regiospecific aziridination of cyclic diene derivatives and subsequent epoxidation with m-CPBA to yield cis-aziridino epoxides as major products. The second strategy utilizes regiospecific epoxidation of cyclic diene derivatives followed by Sharpless aziridination to provide exclusively trans-aziridino epoxides. Synthesis of both enantionters of cis-aziridino epoxides from (R)-(-)- and (S)-(+)-carvones are also reported.

Item Type: Journal Article
Publication: Journal Of Organic Chemistry
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 08 Apr 2009 05:49
Last Modified: 19 Sep 2010 04:58
URI: http://eprints.iisc.ac.in/id/eprint/17788

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