91658-08-1Relevant articles and documents
An efficient protocol for the oxidative hydrolysis of ketone SAMP hydrazones employing SeO2 and H2O2 under buffered (pH 7) conditions
Smith III, Amos B.,Liu, Zhuqing,Simov, Vladimir
experimental part, p. 3131 - 3134 (2010/03/24)
An effective oxidative protocol for the liberation of ketones from SAMP hydrazones employing peroxyselenous acid under aqueous buffered conditions (pH 7) has been developed. The procedure proceeds without epimerization of adjacent stereocenters or dehydration, in representative SAMP alkylation and aldol reaction adducts, respectively.
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
