Tetrahedron 2018-04-11

Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C─N coupling reaction of aryl halides and α-aminoamides

Xiangting Min, Xiaoyu Li, Yu Wang, Yawen Dong, Jingjing Tang, Jing Wang, Jianhui Liu

Index: 10.1016/j.tet.2018.03.003

Full Text: HTML

Abstract

A DMEDA-promoted and copper-catalyzed approach has been designed for the coupling of aryl halides and chiral α-aminoamides to afford a range of functionalized chiral α-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.

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