Chemistry of hydrocarbon compounds – Plural serial diverse syntheses – To produce alicyclic
Patent
1988-10-17
1989-12-12
Davis, Curtis R.
Chemistry of hydrocarbon compounds
Plural serial diverse syntheses
To produce alicyclic
585328, 585357, 585638, C07C 132
Patent
active
048869244
ABSTRACT:
A process for the stereospecific synthesis of [E] alkenes from enamines comprising the steps of hydroborating the enamine; esterifying the organoborane so formed and oxidizing the boronic ester in the presence of hydrogen peroxide and in the absence of added base under conditions sufficient to form the [E] alkene in high yield.
REFERENCES:
Christian T. Goralski et al., "Stereospecific Synthesis of Pure [Z]-and [E]-Alkenes from Enamines via Hydroboration," presented to National American Chemical Society Meeting, Toronto, Canada (Jun. 1988).
Christian T. Goralski et al., "Hydroboration. 81. Synthesis of 2-(Dialkylamino)boronic Esters and Acids via Hydroboration of Enamines. A Convenient Preparation of .beta.-Dialkylamino Alcohols," The Journal of Organic Chemistry, vol. 52, 1987, pp. 4014-4019.
J. W. Lewis et al., "Hydrogenolysis of Enamines. Part II. Hydroboration-Protonolysis," J. Chem. Soc. (B) Phys. Org., 1969, pp. 863-867.
J. W. Lewis et al., "Alkenes from Enamines via Hydroboration," Tetrahedron Letters No. 30, 1964, pp. 2039-2042.
Daniel J. Pasto et al., "Transfer Reactions Involving Boron. IX. Mechanism of Product Formation in the Hydroboration of Vinyl Halides," J. Org. Chem., vol. 31, Sep. 1966, pp. 2773-2777.
Daniel J. Pasto et al., "Transfer Reactions Involving Boron. X. The Stereochemistry of Eliminations Involving .beta.-Substituted Organoboranes," J. Org. Chem., vol. 31, Sep. 1966, pp. 2777-2784.
Gerald L. Larson et al., "A Synthesis of Olefins via Hydroboration of Cyclic Trimethylsilyl Enol Ethers," Tetrahedron Letters No. 46, 1975, pp. 4005-4008.
Gilbert Stork et al., "The Enamine Alkylation and Acylation of Carbonyl Compounds," The Journal of the American Chemical Society, vol. 85, Jan. 20, 1963, pp. 207-222.
Brown Herbert C.
Goralski Christian T.
Singaram Bakthan
Davis Curtis R.
Ruhr Paula Sanders
The Dow Chemical Company
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