Chemistry Letters, Vol.29, No.2, 150-151, 2000
Studies on organosilicon chemistry, No. 150. Tandem aldol-reduction reaction of dimethylsilyl enolates: A new method for stereoselective preparation of 1,3-diols
In the presence of a catalytic amount of TBAF (Bu4NF), dimethylsilyl enolates derived from acyclic ketones reacted with aldehydes to give syn,syn-1,3-diols 7a and 8a with moderate to high diastereoselectivity. The stereochemical outcome can be attributed to a syn-selective aldol reaction and the subsequent 1,2-syn-selective intramolecular reduction.