2432-84-0Relevant articles and documents
Synthesis of multi-functionalized ketones through the fukuyama coupling reaction catalyzed by pearlman’s catalyst: Preparation of ethyl 6-oxotridecanoate: (Tridecanoic acid, 6-oxo-, ethyl ester)
Mori, Yoshikazu,Seki, Masahiko,Aoyama, Naohiro,Shibasaki, Masakatsu
, p. 285 - 294 (2017/10/06)
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Candida antarctica Lipase B Catalysed Kinetic Resolutions: Substrate Structure Requirements for the Preparation of Enantiomerically Enriched Secondary Alcanols
Orrenius, Christian,Oehrner, Niklas,Rotticci, Didier,Mattson, Anders,Hult, Karl,Norin, Torbjoern
, p. 1217 - 1220 (2007/10/02)
The lipase B of the Candida antarctica yeast displays high enantioselectivity in transesterification reactions with chiral secondary alcohols in non-aqueous media.This was exploited to resolve a series of racemates structurally related to 2-octanol, namely 3-hydroxy-1-undecyne, 3-hydroxy-1-nonene, 3-nonanol, 1-chloro-2-octanol, 2-methyl-3-nonanol, 2,2-dimethyl-3-nonanol.The substrates were designed to probe the alcohol binding part of the active site of the lipase.The first four racemates could be resolved to produce compounds of high enantiomeric purity.A lipase catalysed transesterification of 1-chloro-2-octanol was observed. 2-Methyl-3-nonanol and 2,2-dimethyl-3-nonanol did not form any detectable amounts of product ester.The kinetic resolutions of the alcohols were performed with S-ethyl thiooctanoate as the acyl donor.
Resolution of Diols with C2-Symmetry by Lipase Catalysed Transesterification
Mattson, Anders,Oehrner, Niklas,Hult, Karl,Norin, Torbjoern
, p. 925 - 930 (2007/10/02)
S-Ethyl thiooctanoate was used as acyl donor in the transesterification of 2,3-butanediol (1), 2,4-pentanediol (2), and 2,5-hexanediol (3), catalysed by a lipase from Candida antarctica.Mixtures of all stereoisomers were used as substrates in each case. 2,5-Hexanediol was transesterified with high stereoselectivity and the (2S,5S)-2,5-hexanediol was isolated in good yield with >99percent ee.The diester of (2R,5R)-2,5-hexanediol was formed in good yield and was hydrolysed to yield the (2R,5R)-2,5-hexanediol of high enantiomeric excess (>99percent ee).Similar results were obtainedfor 2,4-pentanediol with >99percent ee for both enantiomers.The stereoselectivity for 2,3-butanediol was lower than for 2 and 3, giving 89percent ee for the R,R-enantiomer and 34percent ee for the S,S-enantiomer.