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A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines

Thomas Aubineau, Janine Cossy*

*Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI) - UMR 8231, ESPCI Paris, CNRS, PSL University, 10 rue Vauquelin, 75231 Paris Cedex 05, France, Email: janine.cossyespci.fr

T. Aubineau, J. Cossy, Org. Lett., 2018, 20, 7419-7423.

DOI: 10.1021/acs.orglett.8b03141 (free Supporting Information)



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Abstract

A Pd(0)-catalyzed Tsuji-Trost reaction of vinyloxiranes with amino-alcohols followed in situ by a Fe(III)-catalyzed heterocyclization provides 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines in very good yields and diastereoselectivities.

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Key Words

morpholines


ID: J54-Y2018