Kinetic resolution of trans-2-acetoxycycloalkan-1-ols by lipase-catalysed enantiomerically selective acylation
✍ Scribed by Viktória Bódai; Olivér Orovecz; György Szakács; Lajos Novák; László Poppe
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- English
- Weight
- 215 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0957-4166
No coin nor oath required. For personal study only.
✦ Synopsis
Kinetic resolution of a series of racemic trans-cycloalkane-1,2-diol monoacetates rac-2a-d was performed by enantiomerically selective transesterification with vinyl acetate catalysed by commercial and our own-prepared fungal lipases to yield diacetates (R,R)-3a-d and monoacetates (S,S)-2a-d in high enantiomeric purity. The monoacetates (R,R)-2a-d were also prepared from the racemic diacetates rac-3a-d by lipase-catalysed hydrolysis.
📜 SIMILAR VOLUMES
Lipase B from Candida antarctica (CAL-B) catalyses the highly enantioselective (E > 200) transesterification of some 1-biaryl-2-yl-, -3-yl-, and -4-ylethanols and -propan-1-ols, as well as 1-(o-, m-, and p-pyridylphenyl)ethanols, 6, with vinyl acetate, Kazlauskas rule being obeyed in all cases. meta
Kinetic resolution of racemic 1-(benzofuran-2-yl)ethanols rac-1a-d was performed by lipase-catalyzed enantiomer selective acylation (E100) yielding (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d and (1S)-1-(benzofuran-2-yl)ethanols (S)-1a-d in highly enantiopure form. The degree of enantiomer se
The enantiomer selectivity of the kinetic resolution of phenylethan-l,2-diol [(RS)-I] by sequential acetylation with vinyl acetate in the presence of lipase from Pseudomonas cepacia (Amano PS) was investigated for dependence on the solvent. Optimal conditions for the resolution of (RS)-I are present