Title:
PREPARATION METHOD FOR AND APPLICATION OF 3-SUBSTITUTED CHIRAL SPIRO AMINOPHOSPHINE LIGAND ON PYRIDINE RING
Document Type and Number:
WIPO Patent Application WO/2021/083018
Kind Code:
A1
Abstract:
The present invention relates to a preparation method for and application of a 3-substituted chiral spiro aminophosphine ligand on a pyridine ring. The 3-substituted chiral spiro aminophosphine ligand on a pyridine ring is a compound shown in formula 1, or a racemate or an optical isomer thereof, or a catalytically acceptable salt thereof, and is mainly structurally characterized by having a chiral spiro-dihydro-indene skeleton and a pyridine group. The 3-substituted chiral spiro aminophosphine ligand on a pyridine ring can be synthesized by using a 7-diaryl/alkyl phosphino-7'-amino-1,1'-spiro-dihydro-indene compound with a spiro skeleton as the chiral starting material. The 3-substituted chiral spiro aminophosphine ligand on a pyridine ring forms a complex with a transition metal (iridium) salt, and the complex can be used for catalyzing asymmetric catalytic hydrogenation of an alpha-arylamine substituted lactone compound. The 3-substituted chiral spiro aminophosphine ligand on a pyridine ring shows a very high catalytic activity (TON up to 19,000) and enantioselectivity (up to 99% ee), and has practical value.
Inventors:
XIE JIANHUA (CN)
ZHAO QIANKUN (CN)
GU XUESONG (CN)
ZHOU QILIN (CN)
WANG LIXIN (CN)
ZHAO QIANKUN (CN)
GU XUESONG (CN)
ZHOU QILIN (CN)
WANG LIXIN (CN)
Application Number:
PCT/CN2020/122669
Publication Date:
May 06, 2021
Filing Date:
October 22, 2020
Export Citation:
Assignee:
ZHEJIANG JIUZHOU PHARM CO LTD (CN)
International Classes:
B01J31/22; C07F9/58; B01J31/24; C07C67/303; C07C69/608; C07C69/612; C07C69/65; C07C69/734; C07C69/78; C07D307/54; C07D317/60; C07D333/24
Foreign References:
| CN110724164A | 2020-01-24 | |||
| CN109970795A | 2019-07-05 | |||
| CN109970795A | 2019-07-05 | |||
| CN102040625A | 2011-05-04 | |||
| CN102040625A | 2011-05-04 |
Other References:
XIE, JIANHUA ET AL.: "New Progress and Prospects of Transition Metal-Catalyzed Asymmetric Hydrogenation", ACTA CHIMICA SINICA, vol. 70, no. 13, 26 June 2012 (2012-06-26), pages 1427 - 1438, XP055809675
XIE, JIANHUA ET AL.: "New Progress and Prospects of Transition Metal-Catalyzed Asymmetric Hydrogenation", ACTA CHIMICA SINICA, vol. 70, no. 13, 26 June 2012 (2012-06-26), pages 14727 - 1438, XP055809675
YUAN MING-LEI, XIE JIAN-HUA, YANG XIAO-HUI, ZHOU QI-LIN: "Enantioselective Synthesis of Chiral 1,2-Amino Alcohols via Asymmetric Hydrogenation of α-Amino Ketones with Chiral Spiro Iridium Catalysts", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 46, no. 21, STUTTGART, DE., pages 2910 - 2916, XP055809678, ISSN: 0039-7881, DOI: 10.1055/s-0034-1378891
XIE, JIANHUA ET AL.: "New Progress and Prospects of Transition Metal-Catalyzed Asymmetric Hydrogenation", ACTA CHIMICA SINICA, vol. 70, no. 13, 26 June 2012 (2012-06-26), pages 14727 - 1438, XP055809675
YUAN MING-LEI, XIE JIAN-HUA, YANG XIAO-HUI, ZHOU QI-LIN: "Enantioselective Synthesis of Chiral 1,2-Amino Alcohols via Asymmetric Hydrogenation of α-Amino Ketones with Chiral Spiro Iridium Catalysts", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 46, no. 21, STUTTGART, DE., pages 2910 - 2916, XP055809678, ISSN: 0039-7881, DOI: 10.1055/s-0034-1378891
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