Method for directly constructing highly optically active tetrasubstituted allenic acid compounds
AssigneeFudan Univeristy
InventorsShengming Ma, Weifeng Zheng, Hui Qian
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AssigneeFudan Univeristy
InventorsShengming Ma, Weifeng Zheng, Hui Qian
Estimating the term…
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.
A method for preparing optically active axially chiral allenic acid compounds of formula 2 with greater than 90% enantiomeric excess, wherein, in the presence of palladium catalyst, chiral diphosphine ligand, monophosphine ligand and organic phosphoric acid, a tertiary propargyl alcohol with different substituents, carbon monoxide and water undergo asymmetric allylation reaction in an organic solvent through transition metal catalysis, preparing the optically active axially chiral allenic acid compounds in one-step synthesis, the reaction process has the following reaction equation (I):
Dependencies are inferred from the claim text.