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1. 发明授权

US11220484B2 Production of N-substituted aromatic hydroxylamine 有权
公开(公告)号：US11220484B2
公开(公告)日：2022-01-11
申请号：US16481984
申请日：2018-01-30
申请人： SOLVIAS AG
发明人： Heinz Steiner
IPC分类号： C07D231/22 , C07C269/00 , C07D257/06
摘要： An economic, one-step method for the production of N-substituted aromatic hydroxylamines of formula (I) R—N(OH)—C(═O)—(O)R1 (I), with hydrogen, by catalytic hydration with possibly modified hydration catalysts in an aprotic solvent and in the presence of a halogen formic acid ester and in some cases in the presence of a base.

2. 发明授权

US08450501B2 Bidentate chiral ligands for use in catalytic asymmetric addition reactions 有权
标题翻译：用于催化不对称加成反应的双齿手性配体
公开(公告)号：US08450501B2
公开(公告)日：2013-05-28
申请号：US12734696
申请日：2008-11-14
申请人： Benoît Pugin , Matthias Lotz , Heidi Landert , Adrian Wyss , Raphael Aardoom , Björn Gschwend , Andreas Pfaltz , Felix Spindler
发明人： Benoît Pugin , Matthias Lotz , Heidi Landert , Adrian Wyss , Raphael Aardoom , Björn Gschwend , Andreas Pfaltz , Felix Spindler
IPC分类号： C07D333/26
CPC分类号： C07F13/005 , B01J31/1875 , B01J31/2291 , B01J31/2495 , B01J2231/643 , B01J2231/645 , B01J2531/0238 , B01J2531/822 , B01J2531/827 , C07B53/00 , C07B2200/07 , C07C67/303 , C07C67/31 , C07C231/12 , C07C231/18 , C07F9/46 , C07F9/5004 , C07F9/5018 , C07F9/5022 , C07F9/5027 , C07F9/65515 , C07F9/65517 , C07F9/65522 , C07F9/655354 , C07F17/02 , C07C69/34 , C07C69/732 , C07C69/675 , C07C233/47
摘要： 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.
摘要翻译：主要为一种非对映体或纯非对映体形式的混合物形式的式（I）化合物，其中Z 1为C键，仲膦基-P（R）的Z1-QP * R0R1（I） 2; 其中R各自独立地为烃基或杂烃基，或Z1为-P * R0R1基团; Q是二价，非手性芳族基骨架，二价，非手性二茂铁基骨架，任选取代的二价环烷烃或杂环烷骨架，或C 1 -C 4亚烷基骨架。

3. 发明授权

US07435840B2 Method for producing orthometalated and orthosubstituted metallocenes 失效
标题翻译：生产原位金属和原位取代金属茂的方法
公开(公告)号：US07435840B2
公开(公告)日：2008-10-14
申请号：US10582404
申请日：2004-12-10
申请人： Andreas Pfaltz , Matthias Lotz , Marc Schönleber , Benoît Pugin , Martin Kesselgruber , Marc Thommen
发明人： Andreas Pfaltz , Matthias Lotz , Marc Schönleber , Benoît Pugin , Martin Kesselgruber , Marc Thommen
IPC分类号： C07F15/00 , B01J31/00
CPC分类号： C07F9/65848 , C07F17/02
摘要： 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.
摘要翻译：本发明涉及在芳族烃环中具有式（I）结构元件的化合物，其中：M表示-Li，-MgX 3，（C 1 -C 3）烷基）3-Sn-，-ZnX 3或-B（OC 1 -C 3） 4 - 烷基）2 然后可以转化成次膦基。本发明的方法甚至可以大量生产单膦和二膦，这是用作金属络合物的有价值的配体，用作催化剂。对映选择性氢化。

4. 发明授权

US07094907B2 Ligands for asymmetric reactions 失效
标题翻译：不对称反应配体
公开(公告)号：US07094907B2
公开(公告)日：2006-08-22
申请号：US10491184
申请日：2002-10-02
申请人： Ulrich Berens
发明人： Ulrich Berens
IPC分类号： C07F9/02 , C07D333/00 , C07D327/00 , C07C45/00
CPC分类号： C07F15/008 , B01J31/1845 , B01J31/1865 , B01J31/187 , B01J31/226 , B01J31/2471 , B01J2231/321 , B01J2231/323 , B01J2231/52 , B01J2231/643 , B01J2531/80 , B01J2531/821 , B01J2531/822 , B01J2531/824 , B01J2531/827 , B01J2531/828 , B01J2531/845 , B01J2531/847 , C07B53/00 , C07C45/505 , C07F9/6506 , C07F9/65517 , C07F9/655354 , C07F9/65683 , C07F9/65719 , C07F15/00 , C07F15/0073
摘要： The invention relates to a process for the manufacture of bidentate ligands of the formula IA and IIA, characterized in that N,N-(optionally substituted)dialkylamino phosphines bound to an aromatic carbon are lithiated in ortho-position and the lithiated compounds are further converted to said bidentate ligands: wherein X1 is NR, O or S; X2 is CHR1 or CR1; X3 is CHR2 or NR2, or, if X2is CR1, X3 is CR2 or N; and R, R1 and R2 are radicals such as alkyl groups or R1 and R2 together form an annealed ring; Y1*, Y2* and Y1′* are, independently of each other, an element of the fifth group of the periodic table of elements as such or in thioxo or oxo form; Z1*, Z2*, Z3*, Z4*, Z1′*, Z2′* are, independently of each other, for example halogen, hydrogen, or an unsubstituted or substituted moiety selected from radicals such as alkyl groups; the substituents have otherwise the meanings given in the specification; and the ligands are capable of forming metal complexes, which can be used as catalysts in stereoselective synthesis, especially hydrogenation of various organic molecules.
摘要翻译：本发明涉及制备式IA和IIA的二齿配体的方法，其特征在于与邻位连接的与芳族碳键合的N，N-（任选取代的）二烷基氨基膦进一步转化，并且锂化合物进一步转化所述二齿配体：其中X 1是NR，O或S; X 2是CHR 1或CR 1; X 3是CHR 2或NR 2，或者如果X 2是CR 1， N 3，X 3是CR 2 N或N; 和R 1，R 1和R 2是基团，例如烷基或R 1和R 2共同形成退火环; Y 1 *，Y 2 *和Y 1 *彼此独立地是元素周期表第五组元素元素，或硫代或氧代形式; Z 1，Z 2，Z 3，Z 4，Z 1，Z 3， Z 2是独立的，例如卤素，氢或选自基团如烷基的未取代或取代的部分; 取代基另有说明书中给出的含义; 并且配体能够形成金属络合物，其可以用作立体选择性合成中的催化剂，特别是各种有机分子的氢化。

5. 发明授权

US08415488B2 Bidentate secondary phosphine oxide chiral ligands for use in asymmetric addition reactions 失效
标题翻译：用于不对称加成反应的二齿次膦氧化物手性配体
公开(公告)号：US08415488B2
公开(公告)日：2013-04-09
申请号：US12734726
申请日：2008-11-14
申请人： Benoît Pugin , Heidi Landert , Björn Gschwend , Andreas Pfaltz , Felix Spindler
发明人： Benoît Pugin , Heidi Landert , Björn Gschwend , Andreas Pfaltz , Felix Spindler
IPC分类号： C07D333/62
CPC分类号： C07F9/65517 , B01J31/2495 , B01J2231/643 , B01J2231/645 , B01J2531/822 , B01J2531/827 , C07B53/00 , C07B2200/07 , C07C67/303 , C07C67/31 , C07C213/02 , C07C231/12 , C07C231/18 , C07F9/46 , C07F9/5018 , C07F9/5022 , C07F9/655354 , C07C69/34 , C07C69/732 , C07C69/675 , C07C217/08 , C07C233/47
摘要： 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 radical, a C-bonded heterohydrocarbon radical or a ferrocenyl radical, with the proviso that R1 is an achiral ferrocenyl radical when Q is an achiral ferrocenyl base skeleton. Metal complexes of these ligands in a molar ratio of ligand to metal of about 1.3:1 to 0.9:1 are homogeneous catalysts for asymmetric addition reactions, particularly hydrogenations.
摘要翻译：主要以一种对映体或纯对映异构体形式的混合物形式的式I化合物，其中次膦是C键，仲膦基的仲膦-PQ *（= O）HR1（I） P（R）2; 其中R各自独立地为烃基或杂烃基; Q是二价，非手性，芳族碱基骨架，二价，非手性二茂铁碱骨架，任选取代的二价环烷烃或杂环烷骨架，或C 1 -C 4亚烷基骨架，其中碱基骨架的仲膦基直接键合到碳原子，或者在环状基骨架的情况下，直接与碳原子或C 1 -C 4 - 亚烷基直接键合，并且其中的基础骨架将P手性基团-P *（O）HR1键合到碳原子，使得磷原子通过1至7个碳链连接，任选被来自O，S，N，Fe或Si基团的杂原子中断; P *是手性磷原子; 并且R 1是烃基，C键合的杂烃基或二茂铁基，条件是当Q是非手性二茂铁基时，R 1是非手性二茂铁基。配体与金属的摩尔比约为1.3:1至0.9:1的这些配体的金属络合物是用于不对称加成反应，特别是氢化的均相催化剂。

6. 发明授权

US07994355B2 Metallocene-based chiral phosphine or arsine ligands 失效
标题翻译：基于茂金属的手性膦或胂配体
公开(公告)号：US07994355B2
公开(公告)日：2011-08-09
申请号：US10586287
申请日：2005-01-14
申请人： Wei-Ping Chen , John Whittall
发明人： Wei-Ping Chen , John Whittall
IPC分类号： C07F15/02 , C08F4/70 , C08F4/80
CPC分类号： C07F17/02 , B01J31/1845 , B01J31/186 , B01J31/188 , B01J31/189 , B01J31/1895 , B01J31/2295 , B01J31/2404 , B01J31/2409 , B01J31/2452 , B01J31/2457 , B01J31/2495 , B01J2231/645 , B01J2531/0205 , B01J2531/82 , B01J2531/822 , B01J2531/842 , B01J2531/847
摘要： The present invention relates to metallocene-based phosphine ligands having chirality at phosphorus and at least one other element of chirality (planar chirality and/or chirality at carbon); and to the use of such ligands in asymmetric transformation reactions to generate high enantiomeric excesses of formed compounds. A method for the preparation of ligands according to the invention involving the conversion of the ortho-lithiated substituted metallocene to a phosphine chiral at phosphorus is also disclosed.
摘要翻译：本发明涉及在磷中具有手性和手性的至少一种其他元素（碳的手性和/或手性）的金属茂基膦配体。以及在不对称转化反应中使用这种配体以产生形成的化合物的高对映体过量。还公开了用于制备根据本发明的配体的方法，其涉及将邻位取代的金属茂转化为在磷上手性膦化合物。

7. 发明授权

US07906669B2 Metallocene-based phosphorus chiral phosphines 有权
标题翻译：茂金属磷手性膦
公开(公告)号：US07906669B2
公开(公告)日：2011-03-15
申请号：US11813987
申请日：2006-01-13
申请人： Peter McCormack , Chen Weiping , John Whittall
发明人： Peter McCormack , Chen Weiping , John Whittall
IPC分类号： C08F17/02 , C07F15/00 , C07F9/02 , C07F9/50
CPC分类号： C07C51/36 , C07B53/00 , C07F17/02 , C07C59/66 , C07C59/64
摘要： The present invention concerns a metallocene-based phosphine ligand for use in enantioselective catalysis, the ligand having the Formula (I): Wherein M is a metal; Z is P or As; L is a suitable linker; R1 is selected from alkyl, alkoxy, alkylamino, cycloalkyl, cycloalkoxy, cycloalkylamino carbocyclic aryl, substituted and unsubstituted carbocyclic aryloxy, heteroaryl, heteroaryloxy, carbocyclic arylamino and heteroarylamino; X* is selected from (II): Wherein R, R2 and R3 are independently selected from optionally substituted branched- and straight-chain alkyl, cycloalkyl, heterocycloalkyl, carbocyclic aryl, and heteroaryl.
摘要翻译：本发明涉及用于对映选择性催化的茂金属类膦配体，具有式（I）的配体：其中M是金属; Z是P或As; L是合适的连接体; R 1选自烷基，烷氧基，烷基氨基，环烷基，环烷氧基，环烷基氨基碳环芳基，取代和未取代的碳环芳氧基，杂芳基，杂芳氧基，碳环芳基氨基和杂芳基氨基; X *选自（II）：其中R，R 2和R 3独立地选自任选取代的支链和直链烷基，环烷基，杂环烷基，碳环芳基和杂芳基。

8. 发明授权

US07495123B2 Process for the preparation of enantiomerically enriched beta amino acid derivatives 有权
标题翻译：用于制备对映异构体富集的β氨基酸衍生物的方法
公开(公告)号：US07495123B2
公开(公告)日：2009-02-24
申请号：US11547183
申请日：2005-04-05
申请人： Yi Xiao , Yongkui Sun , Thorsten Rosner , Nelo R. Rivera , Shane W. Krska , Andrew M. Clausen , Joseph D. Armstrong, III , Felix Spindler , Christophe Malan
发明人： Yi Xiao , Yongkui Sun , Thorsten Rosner , Nelo R. Rivera , Shane W. Krska , Andrew M. Clausen , Joseph D. Armstrong, III , Felix Spindler , Christophe Malan
IPC分类号： C07C229/00 , C07C205/00
CPC分类号： C07C227/32 , C07C227/16 , C07C231/18 , C07D213/55 , C07D213/64 , C07D487/04 , C07C229/34 , C07C229/36
摘要： The present invention relates to a process for the efficient preparation of enantiomerically enriched beta amino acid derivatives wherein the amino group is unprotected. The product chiral beta amino acid derivatives are useful in the asymmetric synthesis of biologically active molecules. The process comprises an enantioselective hydrogenation of an amine-unprotected prochiral beta-amino acrylic acid or derivative thereof in the presence of a rhodium metal precursor complexed with a chiral mono- or bisphosphine ligand.
摘要翻译：本发明涉及有效制备对映体富集的β氨基酸衍生物的方法，其中氨基未被保护。产物手性β氨基酸衍生物可用于生物活性分子的不对称合成。该方法包括在与手性单膦或双膦配体配合的铑金属前体的存在下，对胺未未保护的前手性β-氨基丙烯酸或其衍生物进行对映选择性氢化。

9. 发明授权

US08598371B2 Bidentate chiral ligands for use in catalytic asymmetric addition reactions 有权
标题翻译：用于催化不对称加成反应的双齿手性配体
公开(公告)号：US08598371B2
公开(公告)日：2013-12-03
申请号：US13871072
申请日：2013-04-26
申请人： Solvias AG
发明人： Benoit Pugin , Matthias Lotz , Heidi Landert , Adrian Wyss , Raphael Aardoom , Bjorn Gschwend , Andreas Pfaltz , Felix Spindler
IPC分类号： C07F9/28
CPC分类号： C07F13/005 , B01J31/1875 , B01J31/2291 , B01J31/2495 , B01J2231/643 , B01J2231/645 , B01J2531/0238 , B01J2531/822 , B01J2531/827 , C07B53/00 , C07B2200/07 , C07C67/303 , C07C67/31 , C07C231/12 , C07C231/18 , C07F9/46 , C07F9/5004 , C07F9/5018 , C07F9/5022 , C07F9/5027 , C07F9/65515 , C07F9/65517 , C07F9/65522 , C07F9/655354 , C07F17/02 , C07C69/34 , C07C69/732 , C07C69/675 , C07C233/47
摘要： 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 preparation and use.
摘要翻译：主要为一种非对映异构体或纯非对映异构体形式Z1-QP * R0R1（Ⅰ）的混合物形式的式（I）化合物，其中：Z1是式 - P（R）2，其中R是具有1至18个碳原子并且任选被C 1 -C 6烷基，三氟甲基，C 1 -C 6 - 烷氧基，三氟甲氧基，（C 1 -C 6）烷氧基， C 1 -C 4烷基）2氨基，（C 6 H 5）3 Si，（C 1 -C 12烷基）3 Si或卤素; Q选自：（i）任选取代的非手性芳族基团，其中所述非手性芳族基团通过所述非手性芳族基团的碳原子直接键合到Z 1，并通过碳原子直接键合到P * R0R1上; 非手性芳族基团，和（ii）任选取代的C 1 -C 4 - 亚烷基; P *是手性磷原子; R0是甲基; 并且R 1是C-键合的光学富集或光学纯的手性，单环或多环，非芳族烃环; 并准备使用。

10. 发明授权

US07491671B2 Phospholane salts and their use in enantioselective hydrogenation 失效
标题翻译：磷脂盐及其在对映选择性氢化中的应用
公开(公告)号：US07491671B2
公开(公告)日：2009-02-17
申请号：US10556084
申请日：2004-05-07
申请人： Martin Kesselgruber , Marc Thommen
发明人： Martin Kesselgruber , Marc Thommen
IPC分类号： B01J31/00
CPC分类号： B01J31/1845 , B01J2231/643 , B01J2231/645 , B01J2531/023 , B01J2531/821 , B01J2531/822 , B01J2531/827 , C07B53/00 , C07B2200/07 , C07C67/303 , C07F9/65683 , C07F9/65688 , C07C69/34
摘要： 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.
摘要翻译：一种在惰性有机溶剂存在下使金属配合物和二膦反应制备催化剂溶液的方法，其特征在于：a）具有TM8金属作为中心原子的不带电荷或阳离子金属络合物，和b）手性具有一个或两个磷酸基团的二重二膦，其与具有2至4个碳原子的碳链结合并含有选自RCCOO-，RCSO3-，BF4-，PF6-，AsF6-，SbF6-， B（C 6 F 5）4-和B（3,5-双三氟甲基苯基）4-彼此反应，其中组分a）和b）的比例为1:1至1:2，RC为C1-C6 C 5 -C 10 - 卤代环烷基或C 6 -C 10 - 卤代芳基。

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