866003-64-7Relevant academic research and scientific papers
Asymmetric epoxidation of cis-alkenes with arabinose-derived ketones: enantioselective synthesis of the side chain of Taxol
Shing, Tony K.M.,Luk, To,Lee, Chi M.
, p. 6621 - 6629 (2007/10/03)
The ee values of asymmetric epoxidation of cis-ethyl cinnamate 15 with arabinose-derived ketones as catalyst and Oxone as the terminal oxidant were found to increase inversely with the size of the catalyst acetal blocking group. Ketone catalyst
Arabinose-derived ketones as catalysts for asymmetric epoxidation of alkenes
Shing, Tony K. M.,Leung, Gulice Y. C.,Luk, To
, p. 7279 - 7289 (2007/10/03)
Readily available arabinose-derived ketones, containing a tunable butane-2,3-diacetal as the steric blocker, displayed increasing enantioselectivity (up to 90% ee) with the size of the acetal alkyl group in catalytic asymmetric epoxidation of trans-disubstituted and trisubstituted alkenes. The stereochemical communication between our ketone catalysts and the alkene substrates is mainly due to steric effect, and electronic effect involving π-π interaction between phenyl groups of substrate and of catalyst did not appear to be operative in our system.
