Process for producing optically active benzhydrol compounds

Details Process for producing optically active benzhydrol compounds Process for producing optically active benzhydrol compounds

1996-12-24

1998-07-14

Geist, Gary

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

Organic compounds

Oxygen containing

568816, 568817, 568807, 568809, 568812, C07C 3346, C07C 3334, C07C 3521, C07C 3522

Patent

active

057806926

ABSTRACT:
A process for producing a benzhydrol compound (II) which comprises hydrogenating a benzophenone compound (I) in the presence of a hydrogenation catalyst consisting of a transition metal complex, a base and an optically active diamine compound: ##STR1## wherein R.sup.1 to R.sup.10 each represents H, OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkanoyl, etc., R.sup.2 and R.sup.3, and R.sup.8 and R.sup.9 may form --CH.dbd.CH--CH.dbd.CH--, or any two of R.sup.1 to R.sup.9 adjacent to each other may be bonded to thereby form --OCH.sub.2 O-- or --(CH.sub.2).sub.3 --. By using this process, optically active benzhydrol compounds which have a high purity and are useful as, for example, intermediates in the synthesis of drugs can be produced by simple procedures.

REFERENCES:
patent: 3968147 (1976-07-01), Solodar
M.P. Balfe, M.A. Doughty, J. Kenyon, and R. Poplet, Alkyl-Oxygen Fission in Carboxylic Esters. Part II. Derivatives of p-Methoxybenzhydrol. J. Chem. Soc., 1942, 605-611.
D. Seebach, A. K. Beck, S. Roggo, and A. Wonnacott, Enantioselektive Addition von Arylgruppen an aromatische Aldehyde mit Aryltitan-Binaphtol-Derivaten, Chem. Ber., 118, 3673-3682 (1985).
Ji-Tao Wang, X. Fan, X. Feng, and Yi-Min Qian, Studies on Enantioselective Addition of Chiral Titanium Reagents to Aromatic Aldehydes, Synthesis, 1989, 291-292.
Ohkuma et al., J. Am. Soc. 1995, 117, 2675-6.
Journal of the American Chemical Society, vol. 117, No. 9, Mar. 8, 1995, pp. 2675-2676 T. Ohkuma et al, "Practical enantioselective hydrogenation of aromatic ketones".

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