Chiral organoalanes and their organic derivatives via zirconium-

Details Chiral organoalanes and their organic derivatives via zirconium- Chiral organoalanes and their organic derivatives via zirconium-

1997-10-14

1999-12-14

Nazario-Gonzalez, Porfirio

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

Organic compounds

Aluminum containing

556190, 568815, 568897, 568911, C07F 506, C07C 2700

Patent

active

060020377

ABSTRACT:
The present invention describes the Zr-catalyzed asymmetric carboalumination of alkenes to produce chiral alkylalanes that can be converted to various chiral organic compounds, such as isoalkyl alcohols, in highly enantiomeric excess. More particularly, the asymmetric addition of alkylaluminums to terminal alkenes under the influence of a catalyst such as a chiral zirconocene derivative produces chiral alkylaluminums that can be oxidized to 2-alkyl-substituted products (particularly alcohols) in greater than 60% enantiomeric excess. The ee figures can often exceed 95%. The organoalanes produces by the inventive process can be converted to a wide variety of other organic compounds of interest in the production of vitamins, pharmaceuticals and other medicinally and biologically important compounds, including vitamins and antibiotics.

REFERENCES:
Giacomelli et al., J. Org. Chem., vol. 49, pp. 1725-1728, 1984.
Kondakov, Denis Y., and Negishi, Ei-ichi, "Zirconium-Catalyzed Enantioselective Alkylalumination of Monosubstituted Alkenes Proceeding via Noncyclic Mechanism," The Journal of the American Chemical Society, vol. 118, No. 6, 1996, pp. 1577-1578.
Kondakov, Denis Y., and Negishi, Ei-ichi, "Zirconium-Catalyzed Enantioselective Methylalumination of Monosubstituted Alkenes," The Journal of the American Chemical Society, vol. 117, No. 43, 1995, pp. 10771-10772.

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