CHIRAL SPIRO PHOSPHORUS-NITROGEN-SULPHUR TRIDENTATE LIGAND, AND PREPARATION METHOD AND APPLICATION THEREOF

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)

Application Number:

PCT/CN2016/072087

Publication Date:

November 24, 2016

Filing Date:

January 26, 2016

Export Citation:

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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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