公开(公告)号：US11299507B2

公开(公告)日：2022-04-12

申请号：US16770087

申请日：2018-02-08

Applicant: SHENZHEN CATALYS TECHNOLOGY CO., LTD

Inventor： Xumu Zhang ,  Genqiang Chen ,  Jiaming Huang

IPC: C07F15/00 ,  B01J31/22 ,  B01J31/24 ,  C07C51/36 ,  C07F9/6561

Abstract: The present invention relates to the technical field of chiral synthesis, and specifically provides a new type of oxa-spirodiphosphine ligands. The bisphosphine ligand is prepared with oxa-spirobisphenol as a starting material after triflation, palladium catalyzed coupling with diaryl phosphine oxide, reduction of trichlorosilane, further palladium catalyzed coupling with diaryl phosphine oxide, and further reduction of trichlorosilane. The oxa-spiro compound has central chirality, and thus includes L-oxa-spirodiphosphine ligand and R-oxa-spirodiphosphine ligand. The racemic spirodiphosphine ligand is capable of being synthesized from racemic oxa-spirobisphenol as a raw material. The present invention can be used as a chiral ligand in the asymmetric hydrogenation of unsaturated carboxylic acids. The complex of the ligand with ruthenium can achieve an enantioselectivity of greater than 99% in the asymmetric hydrogenation of methyl-cinnamic acid.

公开(公告)号：US12071444B2

公开(公告)日：2024-08-27

申请号：US17689925

申请日：2022-03-08

Applicant: SHENZHEN CATALYS TECHNOLOGY CO., LTD

Inventor： Xumu Zhang ,  Genqiang Chen ,  Jiaming Huang

IPC: C07F15/00 ,  B01J31/22 ,  B01J31/24 ,  C07C51/36 ,  C07F9/6561

CPC classification number: C07F15/0046 ,  B01J31/2213 ,  B01J31/249 ,  C07C51/36 ,  C07F9/6561 ,  B01J2231/645 ,  B01J2531/821 ,  C07B2200/07

Abstract: The present invention relates to the technical field of chiral synthesis, and specifically provides the synthesis and use of a new type of oxa-spirodiphosphine ligands. The bisphosphine ligand is prepared with oxa-spirobisphenol as a starting material after triflation, palladium catalyzed coupling with diaryl phosphine oxide, reduction of trichlorosilane, further palladium catalyzed coupling with diaryl phosphine oxide, and further reduction of trichlorosilane. The oxa-spiro compound has central chirality, and thus includes L-oxa-spirodiphosphine ligand and R-oxa-spirodiphosphine ligand. The racemic spirodiphosphine ligand is capable of being synthesized from racemic oxa-spirobisphenol as a raw material. The present invention can be used as a chiral ligand in the asymmetric hydrogenation of unsaturated carboxylic acids. The complex of the ligand with ruthenium can achieve an enantioselectivity of greater than 99% in the asymmetric hydrogenation of methyl-cinnamic acid.