ol5b02032_si_002.cif (24.98 kB)

Enantioselective Rh(I)-Catalyzed Addition of Arylboronic Acids to Cyclic Ketimines

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posted on 20.11.2015, 00:00 by Jongrock Kong, Mark McLaughlin, Kevin Belyk, Ryan Mondschein
A method for the enantioselective synthesis of chiral α-tertiary amines via Rh-catalyzed 1,2-addition of arylboronic acids to cyclic ketimines is described. The products are efficiently accessed in good yields and excellent enantioselectivities using a commercially available chiral ligand. The reaction scope includes vinyl, aryl, and heteroarylboronic acids with yields ranging from 40% to 99% and enantiomeric excesses from 88% to 99%. Conversion of an addition product into an α,α-diaryl-substituted amino acid is also demonstrated.