Sumika Fine Chemicals, Co.,ltd.

Sumitomo Chemical Company, Limited

Azusa Fujiwara

Gohfu Suzukamo

Kenji Saito

Yukio Yoneyoshi

Norio Kometani

The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4). The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral ketone with, an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.

Process for producing optically active carbinols

The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4). The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral keytone with an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.

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).

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Kawachinagano, Japan

Azusa Fujiwara