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Direct functionalization of labile alkoxyamines

Abstract : Direct esterification of a labile alkoxyamine (RRNOR3)-R-1-N-2, 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. (C) 2012 Elsevier Ltd. All rights reserved.
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Submitted on : Tuesday, February 7, 2017 - 4:34:56 PM
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Paul Brémond, Kuanysh Kabytaev, Sylvain R.A. Marque. Direct functionalization of labile alkoxyamines. Tetrahedron Letters, 2012, 53 (34), pp.4543--4547. ⟨10.1016/j.tetlet.2012.06.049⟩. ⟨hal-01460346⟩



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