Claims
- 1. A ligand of Formula (IV) wherein m and p independently of each other may be equal or different integers in the range of 50 to 150, n and o independently of each other are the same or different integers in the range of 1 to 5 and z and y independent of each other are the same or different integers in the range of 0 to 4, and R1, R2 and R3 independently of each other are equal or different, and R2 and R3 depend from n variable, H, (C1-C5)-alkyl, linear or branched, (C3-C8)-cycloalkyl, aryl, aralkyl, alklaryl or (C1-C8)-alkylalkoxy, linear or branched, and wherein R2 and R3 additionally depend from the variable o and R is a residue selected from the group consisting of Formula (II) and (III)
- 2. A process for the preparation of a ligand of Formula (IV) wherein m and p independently of each other may be equal or different integers in the range of 50 to 150, n and o independently of each other are the same or different integers in the range of 1 to 5 and z and y independent of each other are the same or different integers in the range of 0 to 4, and R1, R2 and R3 independently of each other are equal or different, and R2 and R3 depend from n variable, H, (C1-C5)-alkyl, linear or branched, (C3-C8)-cycloalkyl, aryl, aralkyl, alklaryl or (C1-C8)-alkylalkoxy, linear or branched, and wherein R2 and R3 additionally depend from the variable o, which comprises esterifying intermediate products of Formula (VI), and R is a residue selected from the group consisting of Formula (II) and (III) wherein R′ stands for H, (C1-C5)-alkyl, linear or branched chain, (C3-C8)-cycloalkyl, aryl, aralkyl or alkylaryl with a compound of Formula (VII), wherein m, n and z as well as R1, R2 and R3 have the meanings given for (IV).
- 3. The process in accordance to claim 2 which comprises producing the intermediate products of Formula (VI) by the reaction of compounds of Formula (IX) wherein R is a residue of Formula (II) or (III) with a compound of Formula (X) in the presence of catalytic amounts of palladium and subsequently splitting the silyl group by reaction with a fluoride containing reagent.
- 4. The process according to claim 2 wherein the catalytically active palladium has the oxidation level ±0 and is complexed with a triphenyl phosphine or triphenyl phosphite ligand.
- 5. The process according to claim 3, wherein the catalytically active palladium is a compound of Formula (XI)[Pd(PPH3)4] (XI).
- 6. The process in accordance with claim 2 wherein the silyl group splitting reagent is a tetraalkyl ammonium fluoride.
- 7. A process for the catalytic enantioselective dihydroxylation of double bonds in a solvent in the presence of an oxidizing agent wherein the ligands are selected from the group consisting of compounds of Formula (IV) wherein m and p independently of each other may be equal or different integers in the range of 50 to 150, n and o independently of each other are the same or different integers in the range of 1 to 5 and z and y independent of each other are the same or different integers in the range of 0 to 4, and R1, R2 and R3 independently of each other are equal or different, and R2 and R3 depend from n variable, H, (C1-C5)-alkyl, linear or branched, (C3-C8)-cycloalkyl, aryl, aralkyl, alklaryl or (C1-C8)-alkylalkoxy, linear or branched, and wherein R2 and R3 additionally depend from the variable o and R is a residue selected from the group consisting of Formula (II) and (III)
- 8. The process of claim 7 which comprises precipitating the compound of Formula (IV) after the dihydroxylation, and separating them by filtration from the reaction mixture whereby they can again be introduced into the reaction.
- 9. The process of claim 7 which comprises carrying out the dihydroxylation at a temperature of between −20 and +20° C.
- 10. The process of claim 7 wherein the solvent is a solvent mixture containing one or more solvents of the group: water, alcohols, ethers, ketones esters and halogenated alkanes.
- 11. The process of claim 7 wherein the alcohol is methanol, ethanol, isopropanol, n-propanol, n-butanol, secondary butanol, tert. butanol, isobutanol or n-pentanol, the ether is diethyl ether, tetrahydrofuran, dimethoxy ethane or dioxan, the ketone is acetone, methyl isobutyl ketone, ethyl ketone or diisopropyl ketone, the ester is acetyl acetic ester or acetic ester, and the halogenated alkane is methylene chloride, chloroform or trichloroethylene.
- 12. The process in accordance with claim 7 wherein the oxidizing agent is of potassium hexacyanoferrate or methyl morpholine oxide alone or in the presence of potassium osmate.
- 13. The process in accordance with claim 12 wherein the oxidizing agent is potassium hexacyanoferrate and potassiium osmate.
- 14. The process in a ccordance with claim 12 wherein the oxidizing agent is N-methylmorpoline oxide and potassium osmate.
Priority Claims (1)
Number |
Date |
Country |
Kind |
196 47 899 |
Nov 1996 |
DE |
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RELATED APPLICATIONS
This application is a continuation in part of U.S. Ser. No. 09/308,210 filed Jun. 25, 1999 as a 371 of PCT/EP97/06396 filed Nov. 17, 1997 claiming priority of German Application SN 196 47 889.5 filed Nov. 20, 1996.
Non-Patent Literature Citations (1)
Entry |
Bolm et al. Asymmetric dihydroxylation with MeO-Polyethyleneglycol-bound ligands. Angew. Chem., Int. Ed. Engl., May 1997. |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
09/308210 |
|
US |
Child |
09/504183 |
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US |