Chiral copper amine complexes

Details Chiral copper amine complexes Chiral copper amine complexes

1991-07-15

1992-07-28

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540465, 540541, 544 4, 544 64, 548109, 548402, 556112, 568351, 568388, C07B 3702, C07B 5300, C07D29513

Patent

active

051342383

ABSTRACT:
Disclosed herein is a class of chiral copper-amine complexes of the formula R(L*) CuLi in which L* is selected from: ##STR1## In this formula, R is a transferable ligand, which can be alkyl, aryl or aralkyl. M is a metal ion such as Li, Na, K, Cs, Rb, Be, Mg and other metal ions from the first two columns of the periodic table. R.sub.1 is straight chain alkyl, R.sub.2 is aryl or substituted aryl and R.sub.3 and R.sub.4 form a heterocyclic ring or a substituted heterocyclic ring with 4 to 8 members including oxygen and sulfur.
Such complexes react with .alpha.,.beta.-unsaturated ketones, aldehydes, esters and other carbonyl containing compounds such that R is transferred to the 3 position enantioselectively as shown below. ##STR2## Such complexes react with .alpha.,.beta.-unsaturated ketones in the presence of trialkysilyl halides to give silyl enol ether in which R is substituted in the 3 position as shown below. ##STR3##

REFERENCES:
Bertz et al., New Heterocuprates With Greatly Improved Thermal Stability, J. Am. Chem. Soc. 1982, 104, 5824-5826.
Bertz et al., Factors Governing the Thermal Stability of Organocopper Reagents,, Two New Classes of Heterocuprates With Greatly Improved Stability, J. Chem. Soc. Chem. 1982, 1030-1032.
Bertz et al., Asymmetric Induction with Amidocuprates, J. Org. Chem., 1986, 51, 4953-4959.
Dieter et al., Asymmetric Induction in the Conjugate Addition Reactions of Chiral Organo(hetero)cuprates, J. Am. Chem. Soc. 1987, 109, 2040-2046.
Rossiter et al., Enantioselective Conjugate Addition with Chiral Amidocuprates, Tetrahedron Letter, 1990, 31, 965-968.
Leyendecker et al., Fracteurs Controlant La Reconnaissance Enantioselective de La Chalcone Par Des Cuprates Chiraux, Nouveau Journal de Chimie, 1985, 9, 13-19.
Corey et al., Enantioselective Conjugate Addition of Nationally Designed Chiral Cuprate Reagents to 2-Cycloalkenones, J. Am. Chem. Soc., 1986, 108, 7114-7116.
Villacorta et al., Synthesis and Reactivity of Binuclear Tropocoronand and Related Organocopper (I) Complexes. Catalytic Enantioselective Conjugate Addition of Grignard Reagents to 2-Cyclohexen-1-one. J. Am. Chem. Soc., 1988, 110, 3175-3182.

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