Claims
- 1. A method of stereospecifically producing a compound of formula: or its enantiomer wherein R1 is C1-C6 alkyl and R2 is a hydroxy protective group, which comprises reacting a compound of formula: or its enantiomer, respectively, wherein R1 and R2 are as above and the stereochemistry of both the compound of formula 1AA and the compound of formula 2AA is the same at carbons 1 and 3, respectively, and the stereochemistry of both the compound of formula 1AA* and the compound of formula 2AA* is the same at carbons 1 and 3, respectively, with a fluorinated alcohol having a pKa lower than about 9, in the presence of a palladium catalyst to yield the compound of formula 2AA or 2AA*, respectively.
- 2. The method of claim 1, wherein the reacting is in the presence of a palladium catalyst that is palladium-phosphine catalyst.
- 3. The method of claim 2, wherein the reacting is in the presence of a palladium-phosphine catalyst that is a palladium-triarylphosphine.
- 4. The method of claim 3, wherein the reacting is in the presence of a palladium-triarylphosphine catalyst selected from the group consisting of palladium-triphenylphosphine, palladium-tris(2-methoxyphenyl)phosphine, palladium-tris(3-methoxyphenyl)phosphine, palladium-tris(4-methoxyphenyl)phosphine, palladium-tris(o-tolyl)phosphine, palladium-tris(m-tolyl)phosphine, palladium-tris(p-tolyl)phosphine, palladium-tris(4-fluorophenyl)phosphine, palladium-tris(p-trifluoromethylphenyl)phosphine, and palladium-tris(2-furyl)phosphine.
- 5. The method of claim 1, wherein the reacting is in the presence of a palladium catalyst that is palladium-1,2-bis(diphenylphosphino) ethane.
- 6. The method of claim 1, wherein the reacting is with a fluorinated alcohol selected from the group consisting of: wherein X is phenyl or CF3.
- 7. The method of claim 6, wherein the reacting is with a fluorinated alcohol which is
- 8. The method of claim 6, wherein the reacting is with a fluorinated alcohol which is
- 9. The method of claim 6, wherein the reacting is with a fluorinated alcohol which is:
Parent Case Info
This application claims the priority benefit of provisional application No. 60/150,378 filed Aug. 23, 1999.
Non-Patent Literature Citations (2)
Entry |
Suzuki, M.; Oda, Y.; Noyori, R., J. Am. Chem. Soc., 101, pp. 1623-1625 (1979). |
Shiuey, S.-J.; Kulesha, I.; Baggiolini, E.G.; Uskokovic M.R., J. Org. Chem., 55, pp. 243-247 (1990). |
Provisional Applications (1)
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Number |
Date |
Country |
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60/150378 |
Aug 1999 |
US |