A new synthon for the synthesis of aminoinositol derivatives |
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| Authors: | Nalan Korkmaz Cokol Serdal Kaya Metin Balci |
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| Institution: | 1. Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey;2. Department of Chemistry, Giresun University, 28200 Giresun, Turkey |
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| Abstract: | The regio- and stereoselective synthesis of a new synthon, trans-3,8-dioxatricyclo3.2.1.02,4]octane-6,7-diamine, from 7-oxabicyclo2.2.1]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. |
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| Keywords: | Oxabicycloheptene Aminoinositol Diacylazide Curtius rearrangement Neighbouring group participation |
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