- INTRAMOLECULAR HYDROSILYLATIONS II: THE ANTI-SELECTIVE REDUCTION OF β-HYDROXYKETONES
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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.
- Anwar, S.,Davis, A.P.
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p. 3761 - 3770
(2007/10/02)
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- The Application of Difunctional Organosilicon Compounds to Organic Synthesis; 1,3-Asymmetric Induction in the Reduction of β-Hydroxy-ketones
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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.
- Anwar, Saeed,Davis, Anthony P.
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p. 831 - 832
(2007/10/02)
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