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Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from D-mannitol

Sureshkumar, Devarajulu and Maity, Susama and Chandrasekaran, Srinivasan (2006) Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from D-mannitol. In: Tetrahedron, 62 (43). pp. 10162-10170.

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Abstract

Apractical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive D-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzylidene acetal 3 to form dimesylate 4, which was further converted to monoazides and diazides followed by reduction, mesylation, and cyclization to furnish the required compounds in good yields.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier.
Keywords: Bis-benzylidene acetal;Bis-aziridines;Bis-epoxides;Aziridino epoxides.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 28 May 2008
Last Modified: 19 Sep 2010 04:45
URI: http://eprints.iisc.ernet.in/id/eprint/14062

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