Process for producing optically active...

Details Process for producing optically active... Process for producing optically active...

2006-04-18

2006-04-18

Witherspoon, Sikarl A. (Department: 1621)

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

Organic compounds

Oxygen containing

C568S391000, C568S393000, C568S394000, C568S403000

Reexamination Certificate

active

07030280

ABSTRACT:
The present invention provides a process for producing an optically active β-trifluoromethyl-β-hydroxycarbonyl compound represented by formula (3):comprising a step of reacting a fluoral equivalent represented by formula (1):with a carbonyl compound represented by formula (2):in the presence of an optically active amino acid or a derivative thereof.

REFERENCES:
patent: 6639100 (2003-10-01), Ishii et al.
patent: 2001-226308 (2001-08-01), None
Kitazume et al. Synthesis of fluorinated materials catalyzed by proline or antibody 38C2 in ionic liquid. Journal of Fluorine Chemistry. 2003, vol. 121, p 205-212.
Itoh et al. Dipole Interaction-Controlled Stereoselectivity in Aldol Reaction of alpha-CF3 Enolate with Fluoral. Organic Letters. 2003, vol. 5 (25) p 4807-4809.
Forni, Arrigo et al.: “Stereochemical Control in Yeast Reduction of Fluorinated β-Diketones”, Tetrahedron, England, 1994, vol. 50, No. 41, pp. 11995-12000.
Lin, Jenq Tain et al.: “A Microbially Based Approach for the Preparation of Chiral Molecules Possessing the Trifluoromethyl Group”, Journal of Organic Chemistry, USA, 1987, vol. 52, No. 15, pp. 3211-3217.
Ishii, Akihiro et al.: “Asymmetric Catalytic Friedel-Crafts Reaction of Silyl Enol Ethers with Fluoral: A Possible Mechanism of the Mukaiyama-Aldol Reactions”, Organic Letters, 1999, vol. 1, No. 12, pp. 2013-2016.
Ishii, Akihiro et al.: “Asymmetric Friedel-Crafts reactions of vinyl ethers with fluoral catalyzed by chiral binaphthol-derived titanium catalysts”, Journal of Fluorine Chemistry, Netherlands, 1999, vol. 97, pp. 51-55.
Mikami, Koichi et al.: “Asymmetric Catalysis of Carbonyl-Ene and Aldol Reactions with Fluoral by Chiral Binaphthol-Derived Titanium Complex”, Tetrahedron, England, 1996. vol. 52, No. 1, pp. 85-98.
List, Benjamin et al.: “Proline-Catalyzed Direct Asymmetric Aldol Reactions”, Journal of American Chemical Society, USA, 2000, vol. 122, No. 10, pp. 2395-2396.

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