Abstract
(S)-(+)-2-(α-Hydroxybenzyl)benzimidazole (1) and (S)-(-)-2-benzimidazole-1-ethanol (2) were synthesised and converted to chiral borohydrides which reduced prochiral ketones to the corresponding chiral alcohols in high yields (80 to 100%, e.e. 42 to 95%). This is the first report of sodium borohydride modified by 1,2-amino alcohol.
Notes
Ref 4 of ref. 15 c.
R-(−)-[α]D 25 −4.8° (c 15.3, C6H6 ref. 10c)
Rotation found [α]D 27 −30.5° (c 1.5, CHCl3); Lit R-(−)-[α]D 25 −29° (c 6.0, CHCl3).14a