119968-56-8Relevant academic research and scientific papers
The Application of Difunctional Organosilicon Compounds to Organic Synthesis; 1,3-Asymmetric Induction in the Reduction of β-Hydroxy-ketones
Anwar, Saeed,Davis, Anthony P.
, p. 831 - 832 (1986)
A number of β-hydroxy-ketones were reduced to anti-1,3-diols with diastereoisomeric excesses exceeding 95percent, by a method involving presumed intramolecular transfer of hydrogen from a silicon atom to the carbonyl carbon.
INTRAMOLECULAR HYDROSILYLATIONS II: THE ANTI-SELECTIVE REDUCTION OF β-HYDROXYKETONES
Anwar, S.,Davis, A.P.
, p. 3761 - 3770 (2007/10/02)
A study was made of the synthesis and intramolecular hydrosilylation of silyloxyketones (2) (Sheme 2).It was found that with a variety of Lewis acid catalysts, anti-selective hydrosilylation took place to give (3) and, after desilylation, (5).With SnCl4, the most effective and practical catalyst, ratios (3):(4) ranged between 40:1 and 120:1 for a number of substrates.An explanation for the stereoselectivity is proposed based on (Cl) as a transition state model.The result is an anti-selective reduction of β-hydroxyketones, summarised in Scheme 4.
