Process for producing optically active nitroalcohols

Details Process for producing optically active nitroalcohols Process for producing optically active nitroalcohols

2005-12-20

2005-12-20

Shippen, Michael L. (Department: 1621)

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

Organic compounds

Oxygen containing

C568S583000, C568S587000, C568S704000, C568S709000

Reexamination Certificate

active

06977315

ABSTRACT:
The present invention relates to a process for producing optically active β-nitroalcohols wherein nitroaldol reactions of aldehydes and nitroalkanes are carried out in the presence of a base and an optically active metal complex catalyst represented by the following formula (c):(where R4, R5, and R6represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an acyl group, an alkoxycarbonyl group, or an aryloxycarbonyl group, and R5and R6may be linked together to form a ring; X* represents a hydrocarbon group having an asymmetric carbon atom or axial asymmetry; M represents a cobalt ion or a chromium ion; and Y represents an anion capable of forming a salt when the valence of M is larger than that of a ligand).

REFERENCES:
patent: 5756790 (1998-05-01), Mukaiyama et al.
patent: 6610889 (2003-08-01), Trost et al.
patent: 6-154618 (1994-06-01), None
patent: 9-151143 (1997-06-01), None
patent: 9-253502 (1997-09-01), None
patent: 9-255631 (1997-09-01), None
Sasai et al., “Basic Character of Rare Earth Metal Alkoxides Utilization in Catalytic C-C Bond-Forming Reactions and Catalytic Asymmetric Nitroaidol Reactions”,J. Am. Chem. Soc., 114, pp. 4418-4420 (1992); American Chemical Society.
Sasai et al., “Catalytic Asymmetric Nitroaldol Reaction: An Efficient Synthesis of (S) Propranolol Using the Lanthanum Binaphthol Complex”,Tetrahedron Letters, 34, No. 5, pp. 855-858 (1993), Pergamon Press Ltd., Great Britain.
Sasai et al., “Efficient Diastereoselective and Enantioselective Nitroaldol Reactions from Prochiral Starting Materials: Utilization of La-Li-6,6′-Disubstituted BINOL Complexes as Asymmetric Catalysts”,J. Org. Chem.60, pp. 7388-7389 (1995), American Chemical Society.
Trost et al., “A Dinuclear Zn Catalyst for the Asymmetric Nitroaldol (Henry) Reaction”,Angew. Chem. Int. Ed.2002, 41, No. 5, pp. 861-863 (2002), Wiley-VCH Verlag GmbH, Germany.
Nishida et al. “Effects of Substituents in the Chelate Ring on the Electronic State of Tetraazamacrocyclic Complexes of Cobalt(II), Nickel(II) and Copper(II)”,Inorganica Chimic Acta, 38, pp. 213-219 (1980), Elsevier Sequoia S.A., Lausanne, Switzerland.
Ann. Chem.297, pp. 57-74 (1897)* no translation.
Z. Chem.8 pp. 30-31 (1968)* no translation.
Z. Chem.8 pp. 392-393 (1968)* no translation.

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