Chemistry of hydrocarbon compounds – Plural serial diverse syntheses – To produce unsaturate
Patent
1988-10-17
1990-01-23
Davis, Curtis R.
Chemistry of hydrocarbon compounds
Plural serial diverse syntheses
To produce unsaturate
585318, 585357, 585638, C07C 132
Patent
active
048959960
ABSTRACT:
Alkenes are prepared by the hydroboration of enamines followed by an elimination reaction to form the alkene. This process has wide applicability and is useful for the stereospecific synthesis of [Z] isomers. It is preferred to use 9-borabicyclo[3.3.1 nonane as the hydroborating agent and to use methanol to catalyze the elimination reaction.
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. 4104-4019.
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.
Purdue Research Foundation
Ruhr Paula Sanders
The Dow Chemical Company
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