Process for producing (R)-styrene oxides

Details Process for producing (R)-styrene oxides Process for producing (R)-styrene oxides

1996-03-29

1998-02-10

Ford, John M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549518, C07D30124, C07D30126

Patent

active

057171165

ABSTRACT:
The present invention provides a process for producing (R)-styrene oxides represented by the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and X are as defined in the specification, which comprises treating a mixture of (R)- and (S)-phenylhalogenomethylcarbinols with a lipase in the presence of a carboxylate to preferentially convert the (S)-phenylhalogenomethylcarbinols, and treating a mixture of the formed carbinol alkylates (3) and (R)-phenylhalogenomethylcarbinols with a base to cyclize the (R)-phenylhalogenomethylcarbinols, and also provides an industrially excellent process for producing (R)-styrene oxides (1) which comprises using a mixture enriched with (R)-phenylhalogenomethylcarbinols as the mixture of (R)- and (S)-phenylhalogenomethylcarbinols (2).

REFERENCES:
patent: 5266485 (1993-11-01), Sawa et al.
Journal of Medicinal Chemistry, 1992, vol. 35, No. 16, pp. 3081-3084.
"Asymmetric Synthesis Using Chirally Modified Borohydrides. Part 3. Enantioselective Reduction of Ketones and Oxime Ethers with Reagents Prepared from Borane and Chiral Amino Alcohols", S. Itsuno et al., Journal Chem. Soc. Perkin Trans. 1985 pp. 2039-2044.
Niedizak, Margolin, Tetrahedron: Asymmetry, 2(2), 1991 pp. 113-122.

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