The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Feb. 04, 2020

Filed:

Jan. 16, 2016
Applicant:

Zhejiang Jiuzhou Pharmaceutical Co., Ltd., Zhejiang, CN;

Inventors:

Qilin Zhou, Tianjin, CN;

Jianhua Xie, Tianjin, CN;

Denghui Bao, Tianjin, CN;

Lixin Wang, Tianjin, CN;

Assignee:

Other;

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
B01J 37/04 (2006.01); C07B 53/00 (2006.01); C07C 29/145 (2006.01); C07C 29/149 (2006.01); C07C 67/31 (2006.01); C07C 69/675 (2006.01); C07C 69/708 (2006.01); C07C 231/12 (2006.01); C07C 231/18 (2006.01); C07C 235/06 (2006.01); C07C 269/06 (2006.01); C07C 271/22 (2006.01); C07F 9/50 (2006.01); C07F 15/00 (2006.01); B01J 31/18 (2006.01); B01J 31/22 (2006.01); C07F 9/6553 (2006.01); B01J 31/24 (2006.01);
U.S. Cl.
CPC ...
C07F 9/5022 (2013.01); B01J 31/189 (2013.01); B01J 31/226 (2013.01); B01J 37/04 (2013.01); C07B 53/00 (2013.01); C07C 29/145 (2013.01); C07C 29/149 (2013.01); C07C 67/31 (2013.01); C07C 69/675 (2013.01); C07C 69/708 (2013.01); C07C 231/12 (2013.01); C07C 231/18 (2013.01); C07C 235/06 (2013.01); C07C 269/06 (2013.01); C07C 271/22 (2013.01); C07F 9/5054 (2013.01); C07F 9/655363 (2013.01); C07F 15/0033 (2013.01); B01J 31/249 (2013.01); B01J 2231/643 (2013.01); B01J 2531/0241 (2013.01); B01J 2531/827 (2013.01);
Abstract

The present invention relates to a chiral spiro phosphine-nitrogen-sulfur (P—N—S) tridentate ligand, preparation method and application thereof. The P—N—S tridentate ligand is a compound represented by Formula I or Formula II, their racemates, optical isomers, or catalytically acceptable salts thereof. The ligand has a primary structure skeleton characterized as a chiral spiro indan skeleton structure with a thio group. The chiral spiro phosphine-nitrogen-sulfur tridentate ligand can be synthesized by reacting racemic or optical active compound 7-diary/alkyl phosphine-7'-amino-1, 1′-spiro-dihydro-indene compound having a spiro-dihydro-indene skeleton as the starting material. The chiral spiro P—N—S tridentate ligand being complex with transition metal salt can be used in an asymmetric catalytic hydrogenation reaction for catalyzing carbonyl compound. In particular, in asymmetric hydrogenation reaction process, being complex with iridium for catalyzing β-alkyl-β-keto ester can obtain a high catalytic activity (a catalyst amount of 0.0002% mol) and high enantioselectivity (up to 99.9% ee) result. So the present invention has a practical value for industrial and commercial production.


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