Stereospecific synthesis of tetrasubstituted acrylic esters

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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560 8, C07C 6976

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051625660

ABSTRACT:
Substantially stereospacific (E)-tetrasubstituted acrylic esters, such as ##STR1## where R is hydrogen alkyl, R.sub.1 is alkyl, aryl or aralkyl, R.sub.2 and R.sub.4 are alkyl, are formed from racemic mixtures of corresponding unsaturated esters and cuprates of the formula (R.sub.3).sub.2 CuX, wherein R.sub.3 is alkyl, aryl or aralkyl, and X is lithium or magnesium halide.

REFERENCES:
patent: 4980377 (1990-12-01), Lafon
Hudrilik et al., Sterospecific Olefin-Forming Elimination Reactions of .beta.-Hydroxylalkylsilanes, J. Am. Chem. Soc., vol. 97, pp. 1464-1468 (1975).
Posner et al., Alkylation of Enolate Ions Generated Regiospecifically via Organocopper . . . Systems, J. Am. Chem. Soc. vol. 97, pp. 107-118 (1975).
J. Mathew, A Novel Route to Substituted Cyclopent-2-3n-1-one; Application to . . . Dihydrojasmone, J. Chem. Soc. Chem. Com., pp. 684-686 (1990).
Peterson, A Carbonyl Olefination Reaction Using Silyl-Substituted Organometallic Compounds, J. Org. Chem., vol. 33, pp. 780-784 (1968).
Jacob Mathew, Synthesis and recations of . . . and Novel Cyclopentenones, J. Org. Chem. vol. 55, pp. 5294-5297 (1990).
Jacob Mathew, Synthesis and Reactions of a .alpha.-Chloro-,.beta.c-unsaturated Esters, J. Org. Chem., vol. 55, pp. 3880-3386 (1990).
Goering, Alkylation of Allylic Derivatives . . . Lithium Dialkylcuprates, J. Org. Chem., vol. 48, pp. 715-721 (1983).
Underiner et al., Cross Coupling of Allylic Derivatives . . . Phenylcooper Reagents, J. Org. Chem. Soc. vol. 54, pp. 3239-3240 (1989).
Fox, Technically Speaking, Cosmetics & Toiletries, vol. 102, pp. 21-24 (1987).
Gage, J. R. and Evans D. A., Organic Synthesis, vol. 68 pp. 77, 83 (1989).
Erickson, T. J., "Asymmetric Synthesis of Darvon Alcohol," J. Org. Chem., vol. 51, pp. 934-935 (1986).
Pohland, A. and Sullivan, H. R., J. Am. Chem. Soc., vol. 77, p. 3400.
Evans, D. A. et al., Stereoselective Aldol Condensations via Boron Enolates, J. Am. Chem. Soc., vol. 103, pp. 3099-3111 (1981).
Parikh, J. R. and Doering, W., J. Am. Chem. Soc. vol. 89, pp. 5505.5507 (1967).
Pohland, et al., J. Org. Chem., vol. 28, p. 2483 (1963).
Brown and Devant, Tetrahedron Letters, 25:5031-5034 (1984).
Evans et al., J. Am. Chem. Soc. pp. 103:2999-3111 (1981).

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