Phospholane salts and their use in enantioselective hydrogenation
AssigneeSolvias AG
InventorsMartin Kesselgruber, Marc Thommen
Life of this patent
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Abstract
Process for preparing a catalyst solution by reacting metal complexes and diphosphines in the presence of an inert organic solvent, which is characterized in that a) an uncharged or cationic metal complex having a TM8 metal as central atom, and b) a salt of a chiral ditertiary diphosphine which has one or two phospholane groups which are bound to a carbon chain having from 2 to 4 carbon atoms and contain anions selected from the group consisting of RCCOO−, RCSO3−, BF4−, PF6−, AsF6−, SbF6−, B(C6F5)4− and B(3,5-bistrifluoromethylphenyl)4−, are reacted with one another, where the ratio of the components a) and b) is from 1:1 to 1:2 and RC is C1-C6-haloalkyl, C5-C10-halocycloalkyl or C6-C10-haloaryl.
Claims20
Process for preparing a catalyst solution by reacting metal complexes and diphosphines in the presence of an inert organic solvent, which is characterized in that
- a) an uncharged or cationic metal complex having a TM8 metal as central atom, and
- b) a salt of a chiral ditertiary diphosphine which has one or two phospholane groups which are bound to a carbon chain having from 2 to 4 carbon atoms and contain anions selected from the group consisting of RcCOO−, RcSO3−, BF4−, PF6−, AsF6−, SbF6−, B(C6F5)4− and
- B(3,5-bistrifluoromethylphenyl)4−,
- are reacted with one another, where the ratio of the components a) and b) is from 1:1 to 1:2 and
- Rc is C1-C6-haloalkyl, C5-C10-halocycloalkyl or C6-C10-haloaryl.
The phospholane salts:
- 1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethylphospholanyl]benzene bistriflate, 1,2-bis[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-dimethylphospholanyl]benzene bistriflate and their enantiomers, bis[(2R,5R)-2,5-dimethylphospholanyl]ethane bistetrafluoroborate and its enantiomers.
Process for hydrogenating heteroatom-carbon and C═C— double bonds of prochiral organic compounds using metal complexes comprising TM8 metals and ditertiary diphosphines which have one or two phospholane groups bound to a carbon chain having from 2 to 4 carbon atoms as homogeneous hydrogenation catalysts, which is characterized in that the catalyst is prepared in situ prior to the hydrogenation by reacting a) an uncharged or cationic metal complex having a TM8 metal as central atom and b) a salt of a chiral ditertiary diphosphine containing one or two phospholane groups which are bound to a carbon chain having from 2 to 4 carbon atoms and contain anions selected from the group consisting of RcCOO−, RcSO3−, BF4−, PF6−, AsF6−, SbF6−, B(C6F5)4− and B(3,5-bistrifluoromethylphenyl)4−, with one another, where the ratio of the components a) and b) is from 1:1 to 1:2 and
- Rc is C1-C6-haloalkyl, C5-C10-halocycloalkyl or C6-C10-haloaryl.
Dependencies are inferred from the claim text.