Title:
CHIRAL SPIRO PHOSPHORUS-NITROGEN-SULPHUR TRIDENTATE LIGAND, AND PREPARATION METHOD AND APPLICATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2016/184160
Kind Code:
A1
Abstract:
The present invention relates to a chiral spiro phosphorus-nitrogen-sulphur (P-N-S) tridentate ligand, and a preparation method and application thereof. The P-N-S tridentate ligand is a compound represented by formula I or formula II, a racemate or optical isomer thereof, or a catalytically acceptable salt thereof, and a primary structural characteristic thereof is a chiral spiro indan skeleton and thio group. The chiral spiro phosphine-nitrogen-sulfur tridentate ligand can be synthesized from a chiral starting material of a 7-diaryl/alkyl phosphino-7'-amino-1,1'-spiro indan compound having a spiro skeleton. The chiral spiro P-N-S tridentate ligand and transition metal salt form a complex which can be used in an asymmetric catalytic hydrogenation reaction for catalyzing a carbonyl compound. In particularly, an iridium complex exhibits a high catalytic activity (a catalyst amount of 0.0002% mol) and enantioselectivity (up to 99.9% ee) in an asymmetric hydrogenation reaction of a β-alkyl-β-keto ester, and has a practical value.
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Inventors:
ZHOU QILIN (CN)
XIE JIANHUA (CN)
BAO DENGHUI (CN)
WANG LIXIN (CN)
XIE JIANHUA (CN)
BAO DENGHUI (CN)
WANG LIXIN (CN)
Application Number:
PCT/CN2016/072087
Publication Date:
November 24, 2016
Filing Date:
January 26, 2016
Export Citation:
Assignee:
ZHEJIANG JIUZHOU PHARM CO LTD (CN)
International Classes:
C07F9/50; B01J31/24; C07B41/02; C07C29/145; C07C67/31; C07C69/675; C07C69/708; C07C231/12; C07C235/06; C07C269/06; C07C271/22
Foreign References:
CN104892672A | 2015-09-09 | |||
CN102040625A | 2011-05-04 | |||
CN101671365A | 2010-03-17 |
Other References:
DENG-HUI BAO ET AL.: "Development of chiral spiro P-N-S ligands for iridium-catalyzed asymmetric hydrogenation of [3-alkyl-beta-ketoesters.", ANGEW. CHEM. INT. ED., vol. 54, 8 June 2015 (2015-06-08), pages 8791 - 8794, XP055330065
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