Process for producing epoxyalcohols of high optical purity

Details Process for producing epoxyalcohols of high optical purity Process for producing epoxyalcohols of high optical purity

1992-04-03

1994-01-11

Robinson, Douglas W.

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

C12P 4100

Patent

active

052780708

ABSTRACT:
A process for enriching or improving the optical purity of an asymmetric epoxidation reaction mixture is provided wherein the chiral epoxy alcohol enantiomer present in minor amounts is effectively separated from the predominant chiral epoxy alcohol enantiomer. The minor enantiomer is converted to an epoxy ester by stereoselective transesterification using a carboxylic acid derivative such as an enol ester and a lipase enzyme. The desired major chiral epoxy alcohol enantiomer is then recovered or reacted in situ to form a chiral epoxy alcohol derivative.

REFERENCES:
patent: 4471130 (1984-09-01), Katsuki et al.
patent: 4594439 (1986-06-01), Katsuki et al.
patent: 4732853 (1988-03-01), Whitesides et al.
patent: 4764628 (1988-08-01), Shum
patent: 4916074 (1990-04-01), Yoshida et al.
patent: 4923810 (1990-05-01), Walts et al.
patent: 5213975 (1993-05-01), Fukusaki et al.
Okumura S, BBA 575:156-165 (1979).
Zaks A, Science 224:1249-51 (1984).
Bevinakatti H, J. Org. Chem 54:2453-55 (1989).
Kirchner et al., J. Am. Chem. Soc. 107, 7072 (1985).
Chen et al., Angew. Chem. Int. Ed. Engl. 28, 695 (1989).
Iwai, Yushi. 42, 88 (1989).
[Baba et al., Agric. Biol. Chem. 52, 2688 (1988)].
Bianchi et al [Tetrahedron Letter 29(20), 2455 (1988)].
Wang et al [J. Am. Chem. Soc. 110, 7200 (1988)].
Klibanov [Acc. Chem. Res. 23, 114 (1990)].
Gao et al [J. Am. Chem. Soc. 109 5765 (1987)].
Jorgensen, Chem. Rev. 89, 431 (1989).
Pfenninger, Synthesis 89 (1986).
Katsuki et al. J. Am. Chem. Soc. 102, 5974 (1980).
Sonnet, J. Org. Chem. 52, 3477 (1987).
Okahata et al, Tetrahedron Letter 29(40), 5133 (1988).
Langrand et al Tetrahedron Letter 26(15), 1857, (1985).
Terao et al, Tetrahedron Letters 29(40), 5173 (1988).
Cambou et al, J. Am. Chem. Soc. 106, 2687 (1984).
Francalanci et al, J. Org. Chem. 52, 5079 (1987).
Belan et al, J. Org. Chem. 52, 256 (1987).

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