Dynamic kinetic resolution of atropisomeric amides.
[reaction: see text] Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82% to 95% and the diastereoselectivities from 2.1:1 to 7.0:1.
Chan
Vincent
V
P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Kim
Jeung Gon
JG
Jimeno
Ciril
C
Carroll
Patrick J
PJ
Walsh
Patrick J
PJ
D000577:Amides / Q000138:chemical synthesis*; D006860:Hydrogen Bonding; D007700:Kinetics; D008968:Molecular Conformation; D013237:Stereoisomerism
D000577:Amides