Chromatography-free enzymatic kinetic resolution of secondary alcohols
Racemic secondary alcohols were resolved by enzymatic esterification using Candida antarctica lipase B (CAL B). After derivatization of the unreacted enantiomer with phthalic anhydride, the resulting phthalic acid monoesters could be easily separated from the corresponding acetates by precipitation and filtration or distillation, thus avoiding laborious column chromatography, which is a major obstacle for large-scale reactions. This method has been successfully applied to the multigram synthesis of enantiopure pyridyl alcohols.
Maywald, Matthias,Pfaltz, Andreas
experimental part
p. 3654 - 3660
(2010/03/25)
Use of (S)-α-methylbenzylamine in the resolution of racemic 2-octanol and α-methylbenzyl alcohol
The title chiral amine can be a convenient substitute for brucine or strychnine in Ingersoll's classical method for the resolution of alcohols via fractional crystallization of their diastereoisomeric phthalate salts.
Reyes,Juaristi
p. 1053 - 1058
(2007/10/02)
ENANTIOFACE-DIFFERENTIATING HYDROGENATION OF 2-ALKANONES OVER MODIFIED RANEY NICKEL
2-Octanone was hydrogenated over tartaric acid-NaBr-modified Raney nickel in the presence of pivalic acid at various temperatures.The hydrogenation at 50 60 deg C gave the best result with regard to the optical yield.Almost 80 percent of the optical yields were attained in the hydrogenations of various 2-alkanones.
Osawa, Tsutomu
p. 1609 - 1612
(2007/10/02)
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