-
1.发明公开公开(公告)号：US20240199521A1
公开(公告)日：2024-06-20
申请号：US18275291
申请日：2022-01-19
Applicant: FUDAN UNIVERSITY
Inventor： Shengming MA , Weifeng ZHENG , Hui QIAN
CPC classification number: C07C51/12 , B01J31/0259 , B01J31/2282 , B01J31/2428 , C07C59/52 , B01J2531/004 , B01J2531/0205 , B01J2531/824
Abstract: Disclosed in the present invention is a preparation method for a tetra-substituted allenoic acid compound based on a palladium catalytic system, that is, a highly optically active allenoic acid compound having axial chirality is directly constructed in one step by reacting tertiary propargyl alcohol, carbon monoxide and water in an organic solvent under the action of a palladium catalyst, a chiral bisphosphine ligand, an organophosphoric acid, and an organic additive, and the theoretical yield can reach 100%. The method of the present invention is simple to operate, the raw materials and reagents are readily available, the reaction conditions are mild, the substrate universality is wide, the functional group compatibility is good, the reaction has high enantioselectivity (77%˜96% ee), and the reaction is well compatible with complex natural products or substrates of a drug molecular skeleton. The highly optically active allenoic acid compound obtained by the present invention can be used as an important intermediate for constructing a γ-butyrolactone compound containing a tetra-substituted chiral quaternary carbon center, tetra-substituted allenol, tetra-substituted allenal, tetra-substituted allenyl ketone, tetra-substituted allenami de and other compounds.
-
2.发明申请公开(公告)号：US20220064096A1
公开(公告)日：2022-03-03
申请号：US17299082
申请日：2019-12-24
Applicant: FUDAN UNIVERSITY
Inventor： Shengming MA , Weifeng ZHENG , Hui QIAN
Abstract: The present invention discloses a method for directly constructing highly optically active tetrasubstituted allenic acid compounds, i.e., a one-step process for directly constructing highly optically active axially chiral tetrasubstituted allenic acid compounds by using tertiary propargyl alcohol, carbon monoxide and water as reactants in an organic solvent in the presence of palladium catalyst, chiral diphosphine ligand, monophosphine ligand and organic phosphoric acid. The method of the present invention has the following advantages: operations are simple, raw materials and reagents are readily available, the reaction conditions are mild, the substrate has high universality, the functional group has good compatibility, and the reaction has high enantioselectivity (90%˜>99% ee). The highly optically active allenic acid compounds obtained by the present invention can be used as an important intermediate to construct γ-butyrolactone compounds containing tetrasubstituted chiral quaternary carbon centers, tetrasubstituted allenic alcohol and other compounds.
-
Search Results
2
records
(took 0.031 seconds)
