Method for producing optically active compound

Details Method for producing optically active compound Method for producing optically active compound

2007-06-14

2009-12-08

Seaman, D. Margaret (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S341500

Reexamination Certificate

active

07629472

ABSTRACT:
The present invention provides a method for producing an optically active β-hydroxy ester compound represented by the general formula:whereinR1represents an optionally substituted hydrocarbon group and the like,R2represents a nitrogen-containing heterocyclic group different from R1, which is represented by the general formula:wherein the ring may be substituted and the like,R3represents an optionally substituted hydrocarbon group and the like,R4and R5represent, the same or different, a hydrogen atom, a halogen atom and the like,the symbol “*” represents an optically active center, which comprises reacting in the presence of a cinchona alkaloid and the like a compound represented by the general formula:wherein R1and R2are as defined above with a compound represented by the general formula:wherein R3, R4and R5are as defined above, and X is a halogen atom.

REFERENCES:
patent: 7247732 (2007-07-01), Yamano et al.
J. M. Andres et al., “Enantioselective Reformatsky Reaction Induced by Chiral Beta-Amino Alcohols”, Tetrahedron, vol. 53, No. 10, pp. 3787-3794, 1997.
Y. Zhang et al., “Enantioselective Synthesis of Beta-Hydroxy Esters by Reformatsky Reactions in Chiral Micelles”, Tetrahedron: Asymmetry, vol. 8, No. 21, pp. 3575-3578, 1997.
M. Guette et al., “Syntheses Asymetrique De Beta-Hydroxyesters par Reaction De Reformatsky en Presence De(-) Sparteine”, Tetrahedron, vol. 29, pp. 3659-3667, 1973.
D. Pini et al., “New Chiral Ligand for Optically Active Beta-Hydroxy Esters Synthesis by Enantioselective Reformatsky Reactions”, Tetrahedron: Asymmetry, vol. 5, No. 10, pp. 1875-1876, 1994.
K. Soai et al., “Enantioselective Reformatsky Reaction with Ketones. Asymmetric Synthesis of Beta-(tert-Hydroxy)esters”, J. Chem. Soc., Chem. Commun., pp. 811-812, 1993.
J. M. Andres et al., “Synthesis of Chiral Alpha, Alpha-Difluoro-Beta-Hydroxy Esters by Enantioselective Reformatsky Reaction”, Synthesis, pp. 1070-1072, 1996.
A. Ojida et al., “Highly Enantioselective Reformatsky Reaction of Ketones: Chelation-Assisted Enantioface Discrimination”, Organic Letters, vol. 4, No. 18, pp. 3051-3054, 2002.
Balan et al., “Selective Formation of α-Methylene-β-amino Acid Derivatives through the Aza Version of the Baylis-Hillman Reaction”, J. Org. Chem., vol. 66, No. 19, pp. 6498-6501, 2001.

Affiliated with

Also associated with

Rating

Method for producing optically active compound does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for producing optically active compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for producing optically active compound will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4112476