%0 Journal Article %A Zhou, Ying %A Murphy, Paul V. %D 2008 %T New Access to 1-Deoxynojirimycin Derivatives via Azide−Alkene Cycloaddition %U https://acs.figshare.com/articles/journal_contribution/New_Access_to_1_Deoxynojirimycin_Derivatives_via_Azide_Alkene_Cycloaddition/2916634 %R 10.1021/ol8014495.s001 %2 https://acs.figshare.com/ndownloader/files/4614955 %K stereoselective intramolecular Huisgen reaction %K allylic strain %K transition state accounts %K DNJ derivatives %K cycloaddition reaction %K New Access %X The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from d-glucono-δ-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction. %I ACS Publications