Process for enantioselective synthesis of single enantiomers...

Details Process for enantioselective synthesis of single enantiomers... Process for enantioselective synthesis of single enantiomers...

2007-10-30

2010-10-12

Shiao, Rei-tsang (Department: 1628)

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

Organic compounds

Amino nitrogen containing

Reexamination Certificate

active

07812193

ABSTRACT:
The invention relates to a method for preparing a sulphoxide compound of formula (I) either as a single enantiomer or in an enantiomerically enriched form, comprising the steps of:a) contacting a pro-chiral sulphide of formula (II) with a metal chiral complex, a base and an oxidizing agent in an organic solvent; and optionallyb) isolating the obtained sulphoxide of formula (I);wherein n, Y, R1, R1a, R2and R2aare as defined herein.

REFERENCES:
patent: 4098824 (1978-07-01), Lafon
patent: 4177290 (1979-12-01), Lafon
patent: 4927855 (1990-05-01), Lafon
patent: 7317126 (2008-01-01), Rebiere et al.
patent: 2002/0043207 (2002-04-01), Singer et al.
patent: 1 260 501 (2002-11-01), None
patent: 02/10125 (2002-02-01), None
patent: 2004/006905 (2004-01-01), None
patent: 2004/060858 (2004-07-01), None
patent: 2004/063149 (2004-07-01), None
The European Search Report dated Feb. 11, 2004 (EP 03 292312).
Abushanab, E., et al., “Stereospecific microbial oxidation of thioethers to sulfoxides. Application to the synthesis of R-mevalonolactone,”Tetrahedron Letts., 1978, 37, 3415-3418.
Berge, S.M., et al., “Pharmaceutical Salts,”J. of Pharm. Sci., 1977, 66(1), 1-19.
Burgess, K., et al., “A facile route to homochiral sulfoxides,”Tetrahedron Letts., 1989, 30(28), 3633-3636.
Cotton, H., et al., “Asymmetric synthesis of esomeprazole,”Tetrahedron: Asymmetry, 2000, 11(18), 3819-3825.
Faber, K.,Biotransformations in Organic Chemistry, 3rdEd., Springer (Ed.), 1997, 103-106 and 220-224.
Fernández, I., et al., “Recent developments in the synthesis and utilization of chiral sulfoxides,”Chem. Review, 2002, A-BC.
Holland, H.L., et al., “An investigation of biotransformation of organic selenides by fungi,”Bioorg. Chem., 1983, 12, 1-7.
Holland, H.L., et al., “The oxidation of organic sulphides byMortierella isabellina. 2. Effects of substituents on the stereochemistry of sulphoxide formation,”Can. J. Chem., 1985, 63, 1118-1120.
Kagan, H.B., et al., “Catalytic asymmetric synthesis; Asymmetric oxidation of sulfides”VCH, 1993, Ojima, I. (Ed.), 1993, 203-226.
Kagan, H.B., “Synthesis of chiral sulfoxides by asymmetric oxidation,”Phosphorus and Sulphur, 1986, 27, 127-132.
Madesclaire, M., “Synthesis of sulfoxides by oxidation of thioethers,”Tetrahedron, 1986, 42(20), 5459-5495.
Ohta, H., et al., “Microbial oxidation of alkyl aryl sulfides to the corresponding optically active sulfoxides,”Agrig. Biol. Chem., 1985, 49, 671-676.
Ohta, H., et al., “Microbial asymmetric oxidation of 2-alkoxyethylsufides and a facile synthesis of chiral vinyl sulfoxide,”Chem. Lett., 1989, 625-628.
Pitchen, P., et al., “An efficient asymmetri oxidation of sulfides to sulfoxides,”J. Am. Chem. Soc., 1984, 106, 8188-8193.
Procter, D.J., “The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones,”J. of Chem. Soc. Perkin Trans, 1998, 641-667.
Secundo,F., et al., “Asymmetric oxidation of sulfides by cyclohexanone monooxygenase,”Tetrahedron: Asymmetry, 1993, 4(9), 1981-1982.
Zhao, S.H., et al., “Asymmetric oxidation of sulfides mediated by chiral titanium complexes: mechanistic and synthetic aspects,”Tetrahedron, 1987, 43(21), 5135-5144.
Zhoa, S.H., et al., Organic Syntheses,John Wiley&Sons, Inc.(Ed.), 1993, vol. VIII, 464-467.
Rajendran et al., 2001, CAS: 135:204429.

Affiliated with

Also associated with

Rating

Process for enantioselective synthesis of single enantiomers... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for enantioselective synthesis of single enantiomers..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for enantioselective synthesis of single enantiomers... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4164990