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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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|
|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|
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