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

A practical 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
Publication:	Tetrahedron
Publisher:	Elsevier
Additional Information:	Copyright of this article belongs to Elsevier.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	03 Aug 2010 10:04
Last Modified:	19 Sep 2010 06:12
URI:	http://eprints.iisc.ac.in/id/eprint/30880

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