Dynamic kinetic resolution of allylic alcohols mediated by ruthenium- and lipase-based catalysts

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2377-2379

  Lee, Donghyun ^a   Huh, Eun A ^a   Kim, Mahn Joo ^a   Jung, Hyun Min ^a   Koh, Jeong Hwan ^a   Park, Jaiwook ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; IMMOBILIZED ENZYME; PROPANOL; RUTHENIUM DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYMOLOGY; KINETICS; METABOLISM; PSEUDOMONAS; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; ENZYMES, IMMOBILIZED; KINETICS; LIPASE; PROPANOLS; PSEUDOMONAS; RUTHENIUM COMPOUNDS; STEREOISOMERISM;

EID: 0034720945     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006159y     Document Type: Article

References (26)

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22. Catalysts 3 and 4 with triethylamine were also effective as the racemization catalysts for the DKR of simple secondary alcohols at higher temperature: Hyun Min Jung, Jeong Hwan Koh, Mahn-Joo Kim, and Jaiwook Park, unpublished results.
23. PCL immobilized on ceramic particles (trade name, Lipase PS-C (type II), Amano, Japan.
24. This was chosen favorably over 3 to minimize the formation of the unwanted ketones.
25. The absolute configuration of the acetylated products is assigned on the basis of the stereospecificity of PCL (Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656) and has been confirmed by comparing the optical rotation of deacetylated 9a with the literature value. See ref 12.
26. 3), for (S)-enantiomer (>95% ee).