An approach to catalytic asymmetric deprotonation of 4-substituted cyclohexanones

Abstract

Lithium-hydrogen interchange between a chiral bidentate amine ((R)- 4b ) and an achiral tridentate lithium amide ( 8) occurs rapidly in situ, favoring the exclusive formation of a chiral bidentate lithium amide ((R)- 5b ) . Based on this finding, catalytic asymmetric deprotonation of 4-substituted cyclohexanones ( 1a∼d) was realized by using less than a stoichiometric amount of (R)- 4b as a chiral auxiliary.