Title:
METHOD FOR PRODUCING AN OPTICALLY ACTIVE 2-METHYL-ALKANE-1-OL FROM THE CORRESPONDING 2-METHYLALK-2-EN-1-AL, COMPRISING CARBONYL-SELECTIVE REDUCTION, ENANTIOSELECTIVE HYDRATION AND LIPASE-CATALYZED, STEREOSELECTIVE ACYLATION IN ORDER TO ENRICH THE DES
Document Type and Number:
WIPO Patent Application WO2006034812
Kind Code:
A3
Abstract:
The invention relates to a method for producing optically active 2-methylalkane-1-ol of general formula (III), comprising the following steps: (i) carbonyl-selective reduction of 2-methylalk-2-en-1-al of general formula (I) to 2-methylalk-2-en-1-ol of general formula (II), (ii) enantioselective hydration of 2-methylalk-2-en-1-ol to give the compound of general formula (III), (iii) increasing the optical yield of the optically active 2-methylalkane-1-ol (III) obtained in step (ii) by way of a lipase-catalyzed acylation reaction, whereby R represents C1-C10 alkyl.
Inventors:
JAEKEL CHRISTOPH (DE)
HEYDRICH GUNNAR (DE)
STUERMER RAINER (DE)
PACIELLO ROCCO (DE)
HEYDRICH GUNNAR (DE)
STUERMER RAINER (DE)
PACIELLO ROCCO (DE)
Application Number:
PCT/EP2005/010240
Publication Date:
July 20, 2006
Filing Date:
September 22, 2005
Export Citation:
Assignee:
BASF AG (DE)
JAEKEL CHRISTOPH (DE)
HEYDRICH GUNNAR (DE)
STUERMER RAINER (DE)
PACIELLO ROCCO (DE)
JAEKEL CHRISTOPH (DE)
HEYDRICH GUNNAR (DE)
STUERMER RAINER (DE)
PACIELLO ROCCO (DE)
International Classes:
C07C29/141; C07C29/17; C12P7/04; C12P41/00
Foreign References:
| EP0529698A2 | 1993-03-03 | |||
| EP0492401A1 | 1992-07-01 |
Other References:
BIANCHI, D. ET AL.: "Anhydrides as Acylating Agents in Lipase-Catalyzed Stereoselective Esterification of Racemic Alcohols", JOURNAL OF ORGANIC CHEMISTRY, vol. 53, 1988, pages 5531 - 5534, XP002274382
BARTH, S. & EFFENBERGER, F.: "Lipase-Catalyzed Resolution of Racemic 2-Alkyl Substituted 1-Alkanols", TETRAHEDRON: ASYMMETRY, vol. 4, no. 5, 1993, pages 823 - 833, XP002380147
HÖGBERG, H.E.: "Approaches to 2-methyl-1-alkanols of high enantiomeric purities via enzyme mediated reactions", NATO ASI SERIES. SERIES C, vol. 381, 1992, pages 399 - 410, XP008063921
BARTH, S. & EFFENBERGER, F.: "Lipase-Catalyzed Resolution of Racemic 2-Alkyl Substituted 1-Alkanols", TETRAHEDRON: ASYMMETRY, vol. 4, no. 5, 1993, pages 823 - 833, XP002380147
HÖGBERG, H.E.: "Approaches to 2-methyl-1-alkanols of high enantiomeric purities via enzyme mediated reactions", NATO ASI SERIES. SERIES C, vol. 381, 1992, pages 399 - 410, XP008063921
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