Cokol, N.K., Kaya, S., Balci, M. (2017)
Tetrahedron Letters, 58(28), 2732-2735
The regio- and stereoselective synthesis of a new synthon, trans-3,8-dioxatricyclo[3.2.1.02,4]octane-6,7-diamine, from 7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate is reported. Transformation of the acid functionalities to acyl azides followed by Curtius rearrangement gave the corresponding trans-diisocyanate, which was reacted with HCl to produce a trans-diamino compound that is a potentially important synthon for the versatile synthesis of aminocyclitols.
Subject Headings: Oxabicycloheptene; Aminoinositol; Diacylazide; Curtius rearrangement; Neighboring group participation
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Type: Journal Article
Serial number: 2301