Method for reducing an .alpha. .beta.-unsaturated ketone

Details Method for reducing an .alpha. .beta.-unsaturated ketone Method for reducing an .alpha. .beta.-unsaturated ketone

1993-12-17

1995-10-17

Ivy, C. Warren

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

544242, 544257, 544264, 544283, 544336, 544353, 549 83, 549305, 549505, 546102, 546139, 546164, 546348, 548127, 548128, 548134, 548125, 548131, 548136, 548146, 548143, 548215, 5483351, 5483731, 548440, 548449, 548469, 548560, C07D23730, C07D33308, C07D27760

Patent

active

054592640

ABSTRACT:
A method for reducing an .alpha.,.beta.-unsaturated ketone of the present invention includes the step of treating the .alpha.,.beta.-unsaturated ketone with a silyl compound in the presence of a Lewis acid and alcohol to selectively reduce the carbonyl group of the .alpha.,.beta.-unsaturated ketone. According to this method, a deoxy-compound can be obtained from the .alpha.,.beta.-unsaturated ketone by selectively reducing the carbonyl group without reducing an .alpha.,.beta.-unsaturated bond.

REFERENCES:
J. H. Brewster et al., "Hydrogenolyses with Chloroaluminum Hydrides. III. Allylic Alcohols", J. Org. Chem., 29, pp. 116-121 (1964).
E. J. Corey et al., "New Reagents for Stereoselective Carbonyl Reduction. An Improved Synthetic Route to the Primary Prostaglandins", J. Am. Chem. Soc., 93, pp. 1491-1493 (1971).
M. P. Doyle et al., "Silane Reductions in Acidic Media. VII. Aluminum Chloride Catalyzed Hydrogen-Halogen Exchange between Organosilanes and Alkyl Halides. An Efficient Hydrocarbon Synthesis", J. Org. Chem., 41, pp. 1393-1396 (1976).
R. O. Hutchins et al., "Sodium Borohydride in Acetic Acid: A Convenient System for the Reductive Deoxygentation of Carbonyl Tosylhydrazones", J. Org. Chem., 43, pp. 2299-2301 (1978).
D. N. Kursanove et al., "Applications of Ionic Hydrogenation to Organic Synthesis", Synthesis, 46, pp. 633-651 (1974).

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