Process for producing optically active carbinols

Details Process for producing optically active carbinols Process for producing optically active carbinols

1995-10-27

1998-11-03

Geist, Gary

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

Organic compounds

Oxygen containing

568814, C07C 3346, C07C 2700

Patent

active

058311327

ABSTRACT:
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.

REFERENCES:
Journal of The Chemical Society, Perkin Transactions 1, No. 8, Aug. 1989; Shinichi Itsuno et al.; "Asymmetric Reduction of Ketoxime O-Alkyl Ethers with Sodium Borohydride.sub.- Lewis Acid", pp. 1548-1549.
Journal of The Chemical Society, Perkin Transactions 1, 1985; Shinichi Itsuno et al.; "Asymmetric Synthesis Using Chirally Modified Borohydrides. Part 3. Enantioselective Reduction of Ketones and Oxime Ethers with Reagents Prepared from Borane and Chiral Amino Alcohols", pp. 2039-2044.

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