Patents by Inventor Andreas Pfaltz
Andreas Pfaltz has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 9181163Abstract: The present invention relates in a first aspect to a process for hydrogenation of ketones having at least a carbon-carbon double bond in the y,8-position to the keto group by hydrogen in the presence of at least one chiral iridium complex of formula (I), where R1 represents a group of formula (II) or (III) or (IV). It has been shown that this process leads to a strong increase in preferential formation of a single isomer. The process is particularly suitable for the hydrogenation of y,8-unsaturated ketones which can be used as flavors and fragrances or for the preparation of vitamin E and its derivatives or of flavors and fragrances.Type: GrantFiled: June 13, 2012Date of Patent: November 10, 2015Assignee: DSM IP ASSETS B.V.Inventors: Marc-André Mueller, Andreas Pfaltz, Jonathan Medlock
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Publication number: 20140249321Abstract: The present invention relates in a first aspect to a process for hydrogenation of ketones having at least a carbon-carbon double bond in the y,8-position to the keto group by hydrogen in the presence of at least one chiral iridium complex of formula (I), where R1 represents a group of formula (II) or (III) or (IV). It has been shown that this process leads to a strong increase in preferential formation of a single isomer. The process is particularly suitable for the hydrogenation of y,8-unsaturated ketones which can be used as flavours and fragrances or for the preparation of vitamin E and its derivatives or of flavours and fragrances.Type: ApplicationFiled: June 13, 2012Publication date: September 4, 2014Applicant: DSM IP ASSETS B.V.Inventors: Marc-André Mueller, Andreas Pfaltz, Jonathan Medlock
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Patent number: 8598371Abstract: Compounds of the formula (I) in the form of a mixture of predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1??(I), wherein: Z1 is a C-bonded, secondary phosphine group of the formula —P(R)2, wherein R is a hydrocarbon radical or O-atom(s)-containing heterohydrocarbon radical having 1 to 18 carbon atoms and optionally substituted by C1-C6-alkyl, trifluoromethyl, C1-C6-alkoxy, trifluoromethoxy, (C1-C4-alkyl)2amino, (C6H5)3Si, (C1-C12-alkyl)3Si or halogen; Q is selected from the group consisting of: (i) an optionally substituted achiral aromatic group, wherein the achiral aromatic group is bonded directly to Z1 through a carbon atom of the achiral aromatic group and bonded directly to P*R0R1 through a carbon atom of the achiral aromatic group, and (ii) an optionally substituted C1-C4-alkylene group; P* is a chiral phosphorus atom; R0 is methyl; and R1 is a C-bonded optically enriched or optically pure chiral, mono- or polycyclic, nonaromatic hydrocarbon ring; and preparatType: GrantFiled: April 26, 2013Date of Patent: December 3, 2013Assignee: Solvias AGInventors: Benoit Pugin, Matthias Lotz, Heidi Landert, Adrian Wyss, Raphael Aardoom, Bjorn Gschwend, Andreas Pfaltz, Felix Spindler
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Publication number: 20130267714Abstract: Compounds of the formula (I) in the form of a mixture of predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1??(I), wherein: Z1 is a C-bonded, secondary phosphine group of the formula —P(R)2, wherein R is a hydrocarbon radical or O-atom(s)-containing heterohydrocarbon radical having 1 to 18 carbon atoms and optionally substituted by C1-C6-alkyl, trifluoromethyl, C1-C6-alkoxy, trifluoromethoxy, (C1-C4-alkyl)2-amino, (C6H5)3Si, (C1-C12-alkyl)3Si or halogen; Q is selected from the group consisting of: (i) an optionally substituted achiral aromatic group, wherein the achiral aromatic group is bonded directly to Z1 through a carbon atom of the achiral aromatic group and bonded directly to P*R0R1 through a carbon atom of the achiral aromatic group, and (ii) an optionally substituted C1-C4-alkylene group; P* is a chiral phosphorus atom; R0 is methyl; and R1 is a C-bonded optically enriched or optically pure chiral, mono- or polycyclic, nonaromatic hydrocarbon ring; and preparType: ApplicationFiled: April 26, 2013Publication date: October 10, 2013Inventors: Benoit PUGIN, Matthias LOTZ, Heidi LANDERT, Adrian WYSS, Raphael AARDOOM, Bjorn GSCHWEND, Andreas PFALTZ, Felix SPINDLER
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Patent number: 8450501Abstract: Compounds of the formula (I), in the form of mixtures comprising predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1 (I) in which Z1 is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals, or Z1 is the —P*R0R1 group; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton.Type: GrantFiled: November 14, 2008Date of Patent: May 28, 2013Assignee: Solvias AGInventors: Benoît Pugin, Matthias Lotz, Heidi Landert, Adrian Wyss, Raphael Aardoom, Björn Gschwend, Andreas Pfaltz, Felix Spindler
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Patent number: 8426617Abstract: The invention relates to the (stereoselective) hydrogenation of carbon-carbon double bonds in compounds having at least one such bond, e.g., isoprenoids, non-cyclic sesquiterpenes, tocomonoenols, tocodienols, tocotrienols or derivatives thereof, as well as to the (stereoselective) hydrogenation of parts/extracts of plant oils containing such tocotrienols or derivatives thereof, in the presence of a chiral Ir complex as the catalyst, whereby preferably one stereoisomer is manufactured in an excess.Type: GrantFiled: December 20, 2005Date of Patent: April 23, 2013Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Frederik Menges, Thomas Netscher, Andreas Pfaltz, Bettina Wustenberg
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Patent number: 8415488Abstract: Compounds of the formula I, in the form of mixtures comprising predominantly one enantiomer or in the form of pure enantiomers, secondary phosphine-Q-P*(?O)HR1 (I) in which secondary phosphine is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton, and in which base skeletons a secondary phosphine group is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group, and in which base skeletons a P-chiral group —P*(O)HR1 is bonded to a carbon atom such that the phosphorus atoms are linked via 1 to 7 atoms of a carbon chain optionally interrupted by heteroatoms from the group of O, S, N, Fe or Si; P* is a chiral phosphorus atom; and R1 is a hydrocarbon radiType: GrantFiled: November 14, 2008Date of Patent: April 9, 2013Assignee: Solvias AGInventors: Benoît Pugin, Heidi Landert, Björn Gschwend, Andreas Pfaltz, Felix Spindler
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Publication number: 20120330030Abstract: Provided is an enantioselective, palladium-catalyzed method for the preparation of ?-amino-?,?-unsaturated carboxylic acid derivatives having the formulas II, III, VII and VIII:Type: ApplicationFiled: September 6, 2012Publication date: December 27, 2012Inventors: Murat Acemoglu, Andreas Pfaltz, Claude Shaerer
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Patent number: 8288566Abstract: Provided is an enantioselective, palladium-catalyzed method for the preparation of ?-amino-?,?-unsaturated carboxylic acid derivatives having the formulas II, III, VII and VIII:Type: GrantFiled: November 16, 2009Date of Patent: October 16, 2012Assignee: Novartis AGInventors: Murat Acemoglu, Andreas Pfaltz, Claude Schaerer
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Publication number: 20110275826Abstract: Chiral compounds of the formula (1), which are optically pure or highly optically enriched in which R0 is C1-C12-alkyl which is unsubstituted or substituted by 1 to 2 C1-C4-alkoxy; cyclo-pentyl or cyclohexyl, which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl or C1-C4-alkoxy; or benzyl, phenyl or naphtyl which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl or C1-C4-fluoroalkoxy, F or Cl, or R0 is —CR5R6OH or —CR5R6OSi(C1-C8-alkyl)3 wherein R5 and R6 are independently selected from the group consisting of H, unsubstituted C1-C12 alkyl, substituted C1-C12 alkyl, unsubstituted C4-C8 cyclo alkyl, substituted C4-C8 cyclo alkyl, unsubstituted aryl, substituted aryl or wherein R5 and R6 can form an unsubstituted 5-6 membered aliphatic carbocycle or a substituted 5-6 membered aliphatic carbocycle, each of R1 and R?1 independently is hydrogen or has the meaning of R0 whereby R1, R?1 and R0 can be same or different, R2 and R3 are independently a C-bonded hydrocarbon radiType: ApplicationFiled: December 22, 2009Publication date: November 10, 2011Inventors: Andreas Pfaltz, Marcus Georg Schrems, Benoît Pugin
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Publication number: 20110263873Abstract: Provided is an enantioselective, palladium-catalyzed method for the preparation of ?-amino-?,?-unsaturated carboxylic acid derivatives having the formulas II, III, VII and VIII:Type: ApplicationFiled: November 16, 2009Publication date: October 27, 2011Inventors: Murat Acemoglu, Andreas Pfaltz, Claude Schaerer
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Patent number: 8008529Abstract: Ligands of the formula (I) secondary phosphine-Q-P(?O)HR1 (I) in the form of mixtures of diastereomers or pure diastereomers, in which secondary phosphine is a secondary phosphine group with hydrocarbon radicals or heterohydrocarbon radicals as substituents; Q is a bivalent bisaryl or bisheteroaryl radical with an axial chiral centre to which the two phosphorus atoms are bonded in the ortho positions to the bisaryl or bisheteroaryl bridge bond, or Q is a bivalent ferrocenyl radical with a planar chiral centre or without a planar chiral centre, to which the phosphorus atom of the secondary phosphine is bonded directly or via a C1-C4-carbon chain to a cyclopentadienyl ring, the —P*(?O)HR1 group is bonded either on the same cyclopentadienyl ring in ortho position to the bonded secondary phosphine or on the other cyclopentadienyl ring; P* is a chiral phosphorus atom, and R1 is a hydrocarbon radical, a heterohydrocarbon radical or a ferrocenyl radical, where R1 is a ferrocenyl radical with a planar chiral centre wType: GrantFiled: May 23, 2007Date of Patent: August 30, 2011Assignee: Solvias AGInventors: Andreas Pfaltz, Yann Ribourdouille, Xiangdong Feng, Balamurugan Ramalingam, Benoît Pugin, Felix Spindler
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Publication number: 20110118482Abstract: Compounds of the formula (I), in the form of mixtures comprising predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1 (I) in which Z1 is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals, or Z1 is the —P*R0R1 group; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton, and in which base skeletons a secondary phosphine group Z1 is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group, and in which base skeletons a P-chiral group —P*R0R1 is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group to a carbon atom such that the phosphorus atoms are linked via 1 to 7 atoms of a carbon chain optionally iType: ApplicationFiled: November 14, 2008Publication date: May 19, 2011Inventors: Benoît Pugin, Matthias Lotz, Heidi Landert, Adrian Wyss, Raphael Aardoom, Bjõrn Gschwend, Andreas Pfaltz, Felix Spindler
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Publication number: 20110098485Abstract: Compounds of the formula I, in the form of mixtures comprising predominantly one enantiomer or in the form of pure enantiomers, secondary phosphine-Q-P*(?O)HR1 (I) in which secondary phosphine is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton, and in which base skeletons a secondary phosphine group is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group, and in which base skeletons a P-chiral group —P*(O)HR1 is bonded to a carbon atom such that the phosphorus atoms are linked via 1 to 7 atoms of a carbon chain optionally interrupted by heteroatoms from the group of O, S, N, Fe or Si; P* is a chiral phosphorus atom; and R1 is a hydrocarbon radiType: ApplicationFiled: November 14, 2008Publication date: April 28, 2011Inventors: Benoît Pugin, Heidi Landert, Björn Gschwend, Andreas Pfaltz, Felix Spindler
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Publication number: 20090171114Abstract: Ligands of the formula (I) secondary phosphine-Q-P(?O)HR1 (I) in the form of mixtures of diastereomers or pure diastereomers, in which secondary phosphine is a secondary phosphine group with hydrocarbon radicals or heterohydrocarbon radicals as substituents; Q is a bivalent bisaryl or bisheteroaryl radical with an axial chiral centre to which the two phosphorus atoms are bonded in the ortho positions to the bisaryl or bisheteroaryl bridge bond, or Q is a bivalent ferrocenyl radical with a planar chiral centre or without a planar chiral centre, to which the phosphorus atom of the secondary phosphine is bonded directly or via a C1-C4-carbon chain to a cyclopentadienyl ring, the —P*(?O)HR1 group is bonded either on the same cyclopentadienyl ring in ortho position to the bonded secondary phosphine or on the other cyclopentadienyl ring; P* is a chiral phosphorus atom, and R1 is a hydrocarbon radical, a heterohydrocarbon radical or a ferrocenyl radical, where R1 is a ferrocenyl radical with a planar chiral centre wType: ApplicationFiled: May 23, 2007Publication date: July 2, 2009Inventors: Andreas Pfaltz, Yann Ribourdouille, Xiangdong Feng, Balamurugan Ramalingam, Benoit Pugin, Felix Spindler
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Patent number: 7435840Abstract: The invention relates to compounds having a structural element of formula (I) in an aromatic hydrocarbon ring, wherein: M represents —Li, —MgX3, (C1-C18-Alkyl)3Sn—, —ZnX3 or —B(O—C1-C4-Alkyl)2; X1 and X2, independent of one another, represent O or N, and C-bound hydrocarbon radicals or heterohydrocarbon radicals are bound to the free bonds of the O and N atoms; group —C?C—, together with C atoms, forms a hydrocarbon aromatic compound and represents X3 Cl, Br or I. The inventive compounds are easily obtained by directly substituting the hydrogen in the ortho position to the P atom with metalation reagents. The metal atoms can then be substituted by a reactive electrophilic compound. The group —P(X1—)(X2—) - - - -(BH3)0,1 can then be converted into a secondary phosphine group. The inventive method enables the production of monophosphines and diphosphines even on a large scale, which are valuable ligands for metal complexes serving as catalysts for, e.g. enantioselective hydrogenations.Type: GrantFiled: December 10, 2004Date of Patent: October 14, 2008Assignee: Solvias AGInventors: Andreas Pfaltz, Matthias Lotz, Marc Schönleber, Benoît Pugin, Martin Kesselgruber, Marc Thommen
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Publication number: 20080039638Abstract: The invention relates to the (stereoselective) hydrogenation of carbon-carbon double bonds in compounds having at least one such bond, e.g., isoprenoids, non-cyclic sesquiterpenes, tocomonoenols, tocodienols, tocotrienols or derivatives thereof, as well as to the (stereoselective) hydrogenation of parts/extracts of plant oils containing such tocotrienols or derivatives thereof, in the presence of a chiral Ir complex as the catalyst, whereby preferably one stereoisomer is manufactured in an excess.Type: ApplicationFiled: December 20, 2005Publication date: February 14, 2008Inventors: Werner Bonrath, Frederik Menges, Thomas Netscher, Andreas Pfaltz, Bettina Wustenberg
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Publication number: 20070149796Abstract: The invention relates to compounds having a structural element of formula (I) in an aromatic hydrocarbon ring, wherein: M represents —Li, —MgX3, (C1-C18-Alkyl)3Sn—, —ZnX3 or —B(O—C1C4-Alkyl)2; X1 and X2, independent of one another, represent O or N, and C-bound hydrocarbon radicals or heterohydrocarbon radicals are bound to the free bonds of the O and N atoms; group —C?C—, together with C atoms, forms a hydrocarbon aromatic compound and represents X3 Cl, Br or I. The inventive compounds are easily obtained by directly substituting the hydrogen in the ortho position to the P atom with metalation reagents. The metal atoms can then be substituted by a reactive electrophilic compound. The group —P(X1—)(X2—) - - - (BH3)0,1 can then be converted into a secondary phosphine group. The inventive method enables the production of monophosphines and diphosphines even on a large scale, which are valuable ligands for metal complexes serving as catalysts for, e.g. enantioselective hydrogenations.Type: ApplicationFiled: December 10, 2004Publication date: June 28, 2007Applicant: SOLVIAS AGInventors: Andreas Pfaltz, Matthias Lotz, Marc Schonleber, Benoit Pugin, Martin Kesselgruber, Marc Thommen
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Publication number: 20070010493Abstract: Compounds of the formulae (I) and (Ia) where X1 is secondary phosphino; R3 is a hydrocarbon radical having from 1 to 20 C atoms, a heterohydrocarbon radical which has from 2 to 20 atoms and at least one heteroatorn selected from the group consisting of O, S, NH and NR, or an —SO2—R radical; R is C1-C18-alkyl, phenyl or benzyl; the radicals R4 are each, or the two radicals R4 together a hydrocarbon radical having from 1 to 20 C atoms; R01 is a hydrocarbon radical having from 1 to 20 C atoms; and R02 and R?o2 are each, independently of one another, a hydrogen atom or independently have the meaning of R01, or R01 and R02 together with the C atom to which they are bound form a three- to eight-membered hydrocarbon or hetero hydrocarbon ring. The compounds are chiral ligands for complexes of metals of transition groups I and VIII which act as catalysts for asymmetric additions, for example of hydrogen, onto prochiral unsaturated organic compounds.Type: ApplicationFiled: August 26, 2004Publication date: January 11, 2007Inventors: Federik Menges, Andreas Pfaltz
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Patent number: 6794532Abstract: Process for enantioselectively hydrogenating prochiral ketones to (S)-alcohols using platinum catalysts in the presence of cinchonines or quinidines as modifiers and in the presence of hydrogen, which is characterized in that the modifiers used are cinchonines unsubstituted in the 3-position, 3-ethylidenyl- or 9-methoxycinchonines or derivatives thereof in which the quinoline ring is replaced by other rings.Type: GrantFiled: April 11, 2003Date of Patent: September 21, 2004Assignee: Solvias AGInventors: Martin Studer, Stephan Burkhardt, Andreas Pfaltz, Christian Exner