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1. CN102040625 - Chiral spiro pyridylamidophosphine ligand compounds and synthesis method and application thereof

Office China
Application Number 201010550836.0
Application Date 19.11.2010
Publication Number 102040625
Publication Date 04.05.2011
Grant Number 102040625
Grant Date 25.09.2013
Publication Kind B
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 31/24
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 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
C07C 33/22
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
33Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
18Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
20monocyclic
22Benzylalcohol; Phenylethyl alcohol
C07C 33/18
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
33Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
18Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
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 Nankai University
浙江九洲药业股份有限公司
Inventors Zhou Qilin
周其林
Xie Jianhua
谢建华
Liu Xiaoyan
刘晓艳
Xie Jianbo
谢剑波
Wang Lixin
王立新
Agents
Title
(EN) Chiral spiro pyridylamidophosphine ligand compounds and synthesis method and application thereof
(ZH) 手性螺环吡啶胺基膦配体化合物与合成方法及其应用
Abstract
(EN)
The invention relates to a chiral spiro pyridylamidophosphine ligand compound and a synthesis method and application thereof. The chiral spiro pyridylamidophosphine compounds are compounds with the structure shown in the formula I or the racemate or optical isomers or salt of the compounds which can be acceptable in catalysis; and the main structural feature of the compounds is a chiral spirobiindane skeleton. The chiral spiro pyridylamidophosphine compounds can be prepared by using 7-diaryl/alkylphosphino-7'-amino-1,1'-spirobiindane with the optical activity of the spiral ring skeleton or substituted 7-diaryl/alkylphosphino-7'-carboxyl-1,1'-spirobiindane as the chiral starting raw material. The chiral spiro pyridylamidophosphine compounds can be used as the chiral ligand in the iridium-catalyzed asymmetric catalytic hydrogenation reaction of carbonyl compound; and the reaction activity is very high, the dosage of the catalyst can be 0.0001mol% and the reaction enantioselectivity is up to 99.9%ee.

(ZH)

本发明涉及一种手性螺环吡啶胺基膦配体化合物与合成方法及其应用。该手性螺环吡啶胺基膦化合物是具有式I结构的化合物,或其消旋体或旋光异构体,或其催化可接受的盐,主要结构特征是具有手性螺二氢茚骨架。该手性螺环吡啶胺基膦化合物可以由具有螺环骨架的光学活性的7-二芳/烷基膦基-7′-氨基-1,1′-螺二氢茚或取代的7-二芳/烷基膦基-7′-羧基-1,1′-螺二氢茚为手性起始原料合成。该手性螺环吡啶胺基膦化合物可作为手性配体用于铱催化的羰基化合物的不对称催化氢化反应中,反应的活性也很高,催化剂的用量可以为0.0001%摩尔,反应的对映选择性达到99.9%ee。