Claims
- 1. A compound of formula I or a salt thereof: wherein each of R1 and R2 is a substituted or a non-substituted aryl group optionally containing one or more heteroatoms wherein said compound of formula I has an enantiomeric excess (ee) >80%.
- 2. A compound according to claim 1 which has an ee >90%.
- 3. A compound according to claim 2 which has an ee >95%.
- 4. A compound according to claim 1 of formula V: wherein, the groups R3 each independently represent halogen, hydroxy, alkyl, cycloalkyl, aryl, alkaryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, amido, amino, nitro, acyl, carboxyl, aryloxycarbonyl, thiol or thioether, and m and n, each independently is 0, 1, 2, 3, 4 or 5.
- 5. A compound according to claim 1 wherein at least one of R1 and R2 is a phenyl group that is substituted at the para position.
- 6. A compound according to claim 4 which is1,3-diphenyl-3-oxopropane-1-sulphonic acid, 3-phenyl-1-(4-methoxyphenyl)-3-oxopropane-1-sulphonic acid, 3-phenyl-1-(4-methylphenyl)-3-oxopropane-1-sulphonic acid, 3-phenyl-1-(4-fluorophenyl)-3-oxopropane-1-sulphonic acid, 3-(4-bromophenyl)-1-phenyl-3-oxopropane sulphonic acid, 3-(4-chlorophenyl)-1-phenyl-3-oxopropane sulphonic acid. 1-phenyl-3-(4-methoxy phenyl)-3-oxopropane-sulphonic acid, or 1-phenyl-3-(4-methylphenyl)-3-oxopropane-1-sulphonic acid, or salts thereof.
- 7. A process for the preparation of a compound according to claim 1 which comprises adding at least one optically active amino-functionalized compound to a mixture of the (d)- and (l)-enantiomers of at least one compound of formula I or the salt thereof in a suitable solvent, whereby a diastereomeric complex is formed of the (d)- or (l)-enantiomer of the compound(s) of formula I and the optically active amino-functionalized compound, and converting the diastereomeric complex into the (d)- or (l)-enantiomer of the compound(s) of formula I or salt(s) thereof.
- 8. The process of claim 7 wherein the amino-functionalized compound is p-methylphenylglycinol or phenylglycine amide.
- 9. A process for the resolution of a mixture of enantiomers of at least one amino-functionalized compound which comprises adding at least one compound of claim 1 in a solvent to the mixture of said enantiomers, to form a diastereomeric complex of the compound of claim 1 and one of said enantiomers andconverting the diastereomeric complex to the (d)- or (l)-enantiomer of said amino-functionalized compound.
- 10. A diastereomeric complex comprising a compound of claim 1 and an enantiomer of an optically active amino-functionalized compound.
- 11. The process of claim 7 wherein the amino functionalized compound is an amine, an amino acid or ester or amide thereof, an amino alcohol or amino thiol.
- 12. The process of claim 9 wherein the amino functionalized compound is an amine, an amino acid or ester or amide thereof, an amino alcohol or amino thiol.
- 13. The complex of claim 10 in which the amino functionalized compound is an amine, an amino acid or ester or amide thereof, an amino alcohol or amino thiol.
- 14. The complex of claim 13 in which the amino functionalized compound is an enantiomer of p-methylphenylglycinol or phenylglycine amide.
- 15. The process of claim 9 wherein the amino-functionalized compound is p-methylphenylglycinol or phenylglycine amide.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1012865 |
Aug 1999 |
NL |
|
Parent Case Info
This is the national stage of PCT/NL 00/00577 filed Aug. 18, 2000, now WO 01/14327.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/NL00/00577 |
|
WO |
00 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO01/14327 |
3/1/2001 |
WO |
A |
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
2455282 |
Thurston |
Nov 1948 |
A |
6235927 |
Vries et al. |
May 2001 |
B1 |
Non-Patent Literature Citations (3)
Entry |
CA:77:90297 abs of Pulp Pap. Mag. Can. by Meshitsuka et al 73(6) pp T165-T168 1972.* |
CA:114:41714 abs of Chemiczne by Rachwal S 32 pp 93-104 1989.* |
CA:93:114288 abs of Helvetica Chimica Acta by Pfoertner Karl 63(3) , pp 664-7 1980. |