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Indexed by:期刊论文

Date of Publication:2018-05-24

Journal:TETRAHEDRON

Included Journals:SCIE

Volume:74

Issue:21

Page Number:2561-2566

ISSN No.:0040-4020

Key Words:Selective cross-coupling; alpha-Aminoamides; Copper-catalyst

Abstract:A DMEDA-promoted and copper-catalyzed approach has been designed for the coupling of aryl halides and chiral alpha-aminoamides to afford a range of functionalized chiral alpha-amino anilides. This method has a higher yield and better reproducibility than those under ligand-free conditions. Of the two amino groups in the same molecule, only the amide NH2 is observed to react, showing high regioselectivity. In addition, no racemization occurs, and the ee can reach 99%. For certain hydroxyl-containing substrates, such as L-tyrosine amide and L-threonine amide, addition of a phase transfer catalyst (15-Crown-5) is necessary for such a transformation. (C) 2018 Elsevier Ltd. All rights reserved.