50498-93-6Relevant articles and documents
Practical synthesis of (S)-(+)-3-octanol by lipase-catalyzed enantioselective acetylation
Yuasa, Yoshifumi,Yuasa, Yoko
, p. 1687 - 1693 (2007/10/03)
(S)-(+)-3-Octanol (S)-1 was prepared in high enantiomeric excess through catalyzed acetylation of racemic alcohol 1 by using lipase from Candida antarctica (Chirazyme L-2) in the presence of vinyl acetate in toluene at 30°C. The pure (S)-1 was obtained in 73% isolated yield with 62% conversion. Moreover, acetate (R)-2 was converted to (S)-1 via mesylation and followed by hydrolysis using sodium bicarbonate solution in 44% yield. Copyright Taylor & Francis Group, LLC.
An amino alcohol ligand for highly enantioselective addition of organozinc reagents to aldehydes: Serendipity rules
Nugent, William A.
, p. 2133 - 2136 (2007/10/03)
(matrix presented) Amino alcohol 4 (or its enantiomer) is prepared in two simple steps. Commercial (1R,2S)-2-amino-1,2-diphenylethanol is dialkylated with bis(2-bromoethyl) ether. Subsequent hydrogenation over 5% Rh on alumina in the presence of morpholine unexpectedly stops at the hexahydro derivative 4. Amino alcohol 4 promotes the enantioselective addition of diethylzinc to aldehydes at room temperature in up to 99% enantiomeric excess.
Enzymic Resolution of (+/-)-Acyclic Alcohols via Asymmetric Hydrolysis of Corresponding Acetates by Microorganisms
Oritani, Takayuki,Yamashita, Kyohei
, p. 2407 - 2412 (2007/10/02)
Asymmetric hydrolysis of (+/-)-1-pentyl-2-propynyl and 1-pentyl-2-propenyl acetates by selected microorganisms produced chiral 1-octyn-3-ol and 1-octen-3-ol, respectively, with high optical purities and acetates of their antipodes.Enantioselectivity of microbial hydrolysis changed with the microorganisms used.Also, (+/-)-1-ethylhexyl acetate was asymmetrically hydrolyzed by microorganisms to give (S)-3-octanol and (R)-1-ethylhexyl acetate of relatively low optical purity and hydrolytic ratio, compared with those of (+/-)-1-pentyl-2-propynyl acetate.
