1989
DOI: 10.1007/bf00262445
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Enzymatic resolution of rac-1,1-dimethyl-1-sila-cyclohexan-2-ol by ester hydrolysis or transesterification using a crude lipase preparation of Candida cylindracea

Abstract: Summary. rac-2-Acetoxy-1,1-dimethyl-1-sila-cyclohexane (rac-2) was synthesized by esterification of rac-1, 1-dimethyl-1 ~sila-cyclohexan-2-ol (rac-1) with acetic anhydride. Enantioselective hydrolysis of rac-2 in aqueous solution, catalysed by a crude Iipase preparation of Candida cylindracea (EC 3.1.1.3), led to the formation of (S)-1 (95% ee). Enantioselective transesterification of rac-1 with triacetin in isooctane, catalysed by the same enzyme preparation, yielded (S)-2 (95% ee), which was separated by chr… Show more

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Cited by 27 publications
(7 citation statements)
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References 14 publications
(10 reference statements)
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“…The results decribed in this paper and elsewhere [1][2][3][4][5][6][7][8][9]12] demonstrate that enantioselective biotransformations may be useful for the synthesis of optically active organosilicon compounds on a preparative scale.…”
Section: Introductionsupporting
confidence: 53%
See 1 more Smart Citation
“…The results decribed in this paper and elsewhere [1][2][3][4][5][6][7][8][9]12] demonstrate that enantioselective biotransformations may be useful for the synthesis of optically active organosilicon compounds on a preparative scale.…”
Section: Introductionsupporting
confidence: 53%
“…The absolute configuration and enantiomeric purity of (R)-2 were determined, after deriva tiza tion with ( R )-a-methoxy-a-trifluoromethyl-phenylacetyl chloride Both enantiomers of 2 were recently prepared in high enantiomeric purity via an enzymatic resolution of rac-2 [12]: ( R )-2 was obtained by enantioselective transesterification of rac-2 with triacetin in isooctane using a crude lipase preparation of Candida cylindracea (E.C. 3.1.1.3), and the corresponding antipode (S)-2 was prepared by enantioselective hydrolysis of rac-2-acetoxy-1,1-dimethyl-1-silacyclohexane in aqueous solution using the same enzyme preparation.…”
Section: Introductionmentioning
confidence: 99%
“…This property can be used to enrich fats from natural sources in essential fatty acids giving an increase in their utility and value [5]. Also very important is the application of lipases in the separation of racemic mixtures in the optic isomers production [6].…”
Section: Introductionmentioning
confidence: 99%
“…7 The general structure of a silatrane ol via two different routes (Fig. 9) [59]. Initially the racemic alcohol was transformed into the racemic acetate ester using acetic anhydride.…”
Section: Free Enzymes and Organosilicon Compoundsmentioning
confidence: 99%