Jordi Bach, Ramon Berenguer, J. Farrás
Nov 1, 1995
Citations
0
Influential Citations
20
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract While the reduction of most α,β-unsaturated ketones with BH 3 :SMe 2 in the presence of ( R )- B -methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine [(R)- 2 ] affords allylic alcohols of the S configuration, that of α,β-unsaturated ketones branched at both the α and α′ positions gives alcohols of the R configuration. Theoretical calculations on complexes of representative enones with BH 3 (6–31G ∗ ) or with BH 3 :(R)- 2 (AM1) may account for the apparent changes in the steric requirements on either side of the CO group.