Novel chiral nitrogen oxygen ligands and synthesis method thereof

Abstract

The invention discloses a series of novel chiral nitrogen oxygen ligands and a synthesis method thereof. According to the invention, simple amino acids, amino acid derivatives proline and Leimi acid,4-aminobutyric acid and tetrahydroisoquiline acid are adopted as raw materials, and a series of key processes are adopted, so that 4-carbon, 6-carbon, 7-carbon and 8-carbon novel chiral nitrogen oxygen ligands, 2-A-propane 3-carbon novel chiral nitrogen oxygen ligands, 2,2-di(B)-propane 3-carbon novel chiral nitrogen oxygen ligands, 1,1-dimethyl cyclopropane 3-carbon novel chiral nitrogen oxygen ligands, 1,1-dimethyl cyclobutane 3-carbon novel chiral nitrogen oxygen ligands, 1,1-dimethyl cyclopentane 3-carbon novel chiral nitrogen oxygen ligands and 1,1-dimethyl cyclohexane 3-carbon novel chiral nitrogen oxygen ligands, p-xylene and m-xylene and o-xylene novel chiral nitrogen oxygen ligands, and p-diethylbenzene, m-diethylbenzene and o-diethylbenzene novel chiral nitrogen oxygen ligands, and other novel chiral nitrogen oxygen ligands are finally synthesized. The above novel chiral nitrogen oxygen molecules can realize high enantioselectivity and high reaction activity in a variety of asymmetric reactions, and have great significance in solving reactions which cannot be completed by existing nitrogen oxygen ligands.

Description

technical field [0001] The invention relates to chiral nitrogen-oxygen ligands used as catalysts in asymmetric catalytic reactions and a preparation method thereof, in particular to simple amino acids and amino acid derivatives proline, remic acid, pipecolic acid and tetrahydroisoquinoline Acid as raw material, through a series of key processes, finally synthesized 4 carbon new chiral nitrogen oxygen, 6 carbon new chiral nitrogen oxygen, 7 carbon new chiral nitrogen oxygen, 8 carbon new chiral nitrogen oxygen, 2-A-propane 3-carbon chiral nitrogen oxide, 2,2-diB-propane 3-carbon chiral nitrogen oxide, 1,1-bis-methylcyclopropane 3-carbon chiral nitrogen oxide, 1,1-bis-methylcyclobutane 3-carbon novel chiral nitrogen oxide, 1,1-bis-methylcyclopentane 3-carbon chiral nitrogen oxide, 1,1-bis-methylcyclohexyl New chiral nitrogen oxides with 3 carbons in alkane, p-xylene, m-xylene and o-xylene and aryl substitution new chiral nitrogen oxides, p-diethylbenzene, m-diethylbenzene and o...

AI Technical Summary

Problems solved by technology

[0012] In summary, based on the existing chiral nitrogen and oxygen, we found that chiral nitrogen and oxygen ligands can be used in Een and aza-Een Reaction, F-C Reaction, Roskamp Reaction, Sulfa-Michael Reaction, MichaelReaction, Oxa-Michael Reaction, Herero-DA Reaction, Haloamination, Henry andaza-Henry Reaction, Hydroxymethylation, Cyanation Reaction, Mannich Reaction, Aldol Reaction, All y lation Reaction, Amination Reaction, α-Chlorination y and photocatalytic reactions, etc. Therefore, it is of great significance to develop new chiral nitrogen-oxygen ligands for asymmetric catalytic reactions and synthesis, and to solve the problem that existing nitrogen-oxygen cannot catalyze reactions.

Images