QUANTUM-CHEMICAL MODELING OF CHIRAL CATALYSIS .13. ON THE ROLE OF BORANE O-ADDUCTS IN THE ENANTIOSELECTIVE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES
V. Nevalainen, QUANTUM-CHEMICAL MODELING OF CHIRAL CATALYSIS .13. ON THE ROLE OF BORANE O-ADDUCTS IN THE ENANTIOSELECTIVE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES, Tetrahedron : asymmetry, 4(9), 1993, pp. 2001-2010
Plausible reactions of Lewis bases (ketones and ethers) with borane O-
adducts of chiral oxazaborolidines used as catalysts in the enantiosel
ective reduction of ketones were investigated by means of ab initio MO
methods. Properties of the O-adducts were found to be different from
those of the corresponding N-adducts. The O-adducts were not able to f
orm complexes with ketones and ethers similar to those of the correspo
nding N-adducts proposed to be essential for the performance of oxazab
orolidines as chiral catalysts in the enantioselective reduction of ke
tones.