14090-58-5Relevant articles and documents
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Neumann,R.C.,Holmes,G.D.
, p. 4317 - 4322 (1968)
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Regio-, Diastereo-, and Enantioselective Synthesis of vic-Diols via α-Silyl Ketones According to the SAMP/RAMP Hydrazone Method
Enders, Dieter,Nakai, Shiro
, p. 219 - 226 (2007/10/02)
α-Silylated ketones 5 or 10 of high enantiomeric purity (ee>=90percent) are easily available by silylation or silylation/alkylation of ketones 1 or 6, resp., according to the SAMP/RAMP hydrazone method.Reduction of 5 or 10 with L-selectride, followed by oxidative cleavage of the C-Si bond, leads to vic-diols 11-13 with high diastereoselectivity (de>=90percent) and without racemization.The stereoselectivity of the reduction depends on the structure of the α-silyl ketones 5 or 10, the reducing reagents, and the solvents used.Key Words: Ketones, α-silyl / vic-Diols, diastereo- and enantioselective synthesis / SAMP/RAMP Hydrazones / L-Selectride reductions