A new method of preparation of optically active a-hydroxy ketone derivatives has been developed. Incubation of (Z)-3-propionyloxy4-benzyloxy-2-pentcne (la) with lipasc OF gave optically pure (R)-cnol propionatc la, which in bun was converted without raccmization to @)-ketone 2a by the aid ofLiAlH4.
โฆ LIBER โฆ
Desymmetrisation of prochiral ketones by catalytic enantioselective hydrolysis of their enol esters using enzymes
โ Scribed by Andrew J Carnell; Jim Barkley; Amarjit Singh
- Book ID
- 104258117
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 195 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Desymmetrisation of 4-cyano-4-phenylcyclohexanone I has been achieved by enzyme-catalysed enantioselective alcoholysis with n-butanol of the derived rscemic enol acetate 2 in tetrahydrofuran. The absolute configuration of the enol acetate (-)-(S)-2 (100% e.e.) obtained was determined by X-my analysis of the camphanyl derivative 7.
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