Preparation of stereoisomers of ketals

Details Preparation of stereoisomers of ketals Preparation of stereoisomers of ketals

1986-06-10

1988-06-07

Lone, Werren B.

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

Organic compounds

Sulfonate esters

568309, 568313, 568315, 568326, 568328, 568323, 562418, 562419, 562490, 562496, C07C13900, C07C 4572

Patent

active

047498048

ABSTRACT:
Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.

REFERENCES:
patent: 3637767 (1972-01-01), Alvarez
Chemical Abstracts, vol. 94, No. 25, Jun. 22, 1981, p. 569, abstract No. 208547g.
Ullmans Encyklopadie der Technischen Chemie, vol. 17, 4th ed., (1979), Weinheim (DE), "Optische aktive Verbindungen," pp. 451-456.
S. Patai: "The Chemistry of the Carbonyl Group,: chp. 6: Carbonyl Syntheses Through Organometallics," (1966), Interscience Publishers, pp. 303-304.
Chemical Abstracts, vol. 92, No. 13, Mar. 31, 1980, p. 634, abstract No. 110735a.
Chemical Abstracts, vol. 89, No. 21, Nov. 20, 1978, p. 584, abstract No. 179745j.
Tetrahedron Letters, vol. 22, No. 43, pp. 4305-4308, (1981).

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