Direct functionalization of labile alkoxyamines

Article abstract of DOI:10.1016/j.tetlet.2012.06.049

Direct esterification of a labile alkoxyamine R¹R ²NOR³, which was previously reported as unsuccessful, is achieved by a Mitsunobu reaction or a nucleophilic substitution. Ester derivatives are obtained under smooth conditions and easily purified. Macrocyclization attempts on ester derivatives were successful for five-membered ring lactones and unsuccessful for 13-membered ring lactones. Moreover, the success of the cyclization was dramatically dependent on the quality of the solution degassing. Poor degassing led to unexpected carbonate alkoxyamine.