Process for the stereoselective production of nitro-enamine comp

Details Process for the stereoselective production of nitro-enamine comp Process for the stereoselective production of nitro-enamine comp

1996-12-13

1998-09-01

Richter, Johann

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549444, C07D40504, C07D31760

Patent

active

058012508

ABSTRACT:
The present invention relates to an asymmetric Michael Addition reaction to produce nitro ketone diasteroisomers with enhanced stereoselectivity.

REFERENCES:
Grant et al., Grant & Hackh's Chemical Dictionary, 5th Ed., McGraw-Hill Book Company, New York, 1987, p. 453.
d'Angelo, J., et al., "A New Strategy for the Enantioselective Synthesis of Intermediates", Unite de Chimie Organique Associee au CNRS, 879-882 (1989).
d'Angelo, J., et al., "The Asymmetric Michael Addition Reactions Using Chiral Imines", Tetrahedron: Asymmetry, 3(4):459-505 (1992).
Desmaele, D., et al., "The Asymmetric Michael Reaction Involving Chiral Imines: Use of Acrylonitrile as Acceptor and Subsequent Functionalization of the Adducts", Tetrahedron: Asymmetry, 5(9):1645-1648 (1994).
Felk, A., et al., "Enantioselective Michael-type Reaction of Chiral Linear .alpha.,.alpha.-Disubstituted Secondary Enamines", Tetrahedron: Asymmetry, 5(8):1459-1462 (1994).
Pfau, M., et al., "Enantioselective Synthesis of Quaternary Carbon Centers through Michael-Type Alkylation of Chiral Imines", American Chemical Society, 107:273-274 (1985).
Pfau, M., et al., "Imine-Enamine Tautomerism-VI.sup.a C-vs N-Alkylation of Imines with Electrophilic Olefins", Tetrahedron, 35(15) 1899-1904 (1979).
Sevin, A., et al., "Toward a Transition-State Model in the Asymmetric Alkylation of Chiral Ketone Secondary Enamines by Electron-Deficient Alkenes. A Theoretical MO Study", American Chemical Society, 51(14):2671-2675 (1986).

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