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1. EP2641910 - CHIRAL SPIRO-PYRIDYLAMIDOPHOSPHINE LIGAND COMPOUND, SYNTHESIS METHOD THEREFOR AND APPLICATION THEREOF

Office European Patent Office
Application Number 11842107
Application Date 18.11.2011
Publication Number 2641910
Publication Date 25.09.2013
Publication Kind B1
IPC
C07F 9/58
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
FACYCLIC, CARBOCYCLIC, OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
9Compounds containing elements of Groups 5 or 15 of the Periodic System
02Phosphorus compounds
547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
553having one nitrogen atom as the only ring hetero atom
576Six-membered rings
58Pyridine rings
B01J 31/18
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31Catalysts comprising hydrides, coordination complexes or organic compounds
16containing coordination complexes
18containing nitrogen, phosphorus, arsenic or antimony
B01J 31/24
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31Catalysts comprising hydrides, coordination complexes or organic compounds
16containing coordination complexes
24Phosphines
C07B 41/02
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
41Formation or introduction of functional groups containing oxygen
02of hydroxy or O-metal groups
C07B 53/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
53Asymmetric syntheses
C07C 29/145
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
29Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
132by reduction of an oxygen-containing functional group
136of C=O containing groups, e.g. -COOH
143of ketones
145with hydrogen or hydrogen-containing gases
CPC
B01J 31/249
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31Catalysts comprising hydrides, coordination complexes or organic compounds
16containing coordination complexes
24Phosphines ; , i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
2442comprising condensed ring systems
249Spiro-condensed ring systems
B01J 31/189
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31Catalysts comprising hydrides, coordination complexes or organic compounds
16containing coordination complexes
18containing nitrogen, phosphorus, arsenic or antimony ; as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
189containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
B01J 2231/643
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
2231Catalytic reactions performed with catalysts classified in B01J31/00
60Reduction reactions, e.g. hydrogenation
64Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
641Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
643of R2C=O or R2C=NR (R= C, H)
B01J 2531/827
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
2531Additional information regarding catalytic systems classified in B01J31/00
80Complexes comprising metals of Group VIII as the central metal
82Metals of the platinum group
827Iridium
C07B 41/02
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
41Formation or introduction of functional groups containing oxygen
02of hydroxy or O-metal groups
C07B 53/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
53Asymmetric syntheses
Applicants ZHEJIANG JIUZHOU PHARMA SCIENCE & TECH CO LTD
Inventors ZHOU QILIN
XIE JIANHUA
LIU XIAOYAN
XIE JIANBO
WANG LIXIN
Designated States
Priority Data 201010550836 19.11.2010 CN
2011082432 18.11.2011 CN
Title
(DE) CHIRALE SPIRO-PYRIDYLAMIDOPHOSPHIN-LIGANDENVERBINDUNG, VERFAHREN ZU IHRER SYNTHESE UND IHRE VERWENDUNG
(EN) CHIRAL SPIRO-PYRIDYLAMIDOPHOSPHINE LIGAND COMPOUND, SYNTHESIS METHOD THEREFOR AND APPLICATION THEREOF
(FR) COMPOSÉ DE LIGAND SPIRO-PYRIDYLAMIDOPHOSPHINE CHIRAL, PROCÉDÉ DE SYNTHÈSE ET APPLICATION DE CELUI-CI
Abstract
(EN)
The present invention relates to a chiral spiro-pyridylamidophosphine ligand compound, synthesis method therefor and application thereof. The chiral spiro-pyridylamidophosphine compound is a compound having a structure of Formula (I), a racemate or optical isomer thereof, or a catalytically acceptable salt thereof, and is mainly characterized by having a chiral spiro-dihydro-indene skeleton in its structure. The chiral spiro-pyridylamidophosphine compound may be synthesized with optical active 7-diaryl/alkylphosphino-7'-amino-1,1'-spiro-dihydro-indene or substituted 7-diaryl/alkylphosphino-7'-amino-1,1'-spiro-dihydro-indene having a spiro-skeleton as chiral starting material. The chiral spiro-pyridylamidophosphine compound may be used as a chiral ligand in asymmetric hydrogenation of a carbonyl compound catalyzed by iridium, in which the reaction activity is very high, the amount of the catalyst may be 0.0001 mol%, and the enantioselectivity of the reaction is up to 99.9%ee.

(FR)
La présente invention concerne un composé de ligand spiro-pyridylamidophosphine chiral, un procédé de synthèse de celui-ci et l'application de celui-ci. Le composé spiro-pyridylamidophosphine chiral est un composé ayant une structure de formule (I), un racémique ou un isomère optique de celui-ci, ou un sel acceptable sur le plan catalytique de celui-ci, et est principalement caractérisé en ce qu'il a un squelette spiro-dihydro-indène dans sa structure. Le composé spiro-pyridylamidophosphine chiral peut être synthétisé avec un 7-diaryl/alkylphosphino-7'-amino-1,1'-spiro-dihydro-indène ou 7-diaryl/alkylphosphino-7'-amino-1,1'-spiro-dihydro-indène substitué optiquement actif ayant un spiro-squelette en tant que matériau de départ chiral. Le composé spiro-pyridylamidophosphine chiral peut être utilisé en tant que ligand chiral dans l'hydrogénation asymétrique d'un composé carbonyle catalysée par l'iridium, dans laquelle l'activité de réaction est très élevée, la quantité du catalyseur peut être de 0,0001 % en moles, et l'énantiosélectivité de la réaction est de jusqu'à 99,9 % en énantiomère.