Chiral spiro monophosphine-oxazoline ligands and preparation method thereof

Abstract

The invention provides chiral spiro monophosphine-oxazoline ligands as well as intermediates and a preparation method thereof. The ligands are structural compounds shown in the following formulas 1, 2and 3 and comprise racemates and optical isomers of the compounds, and m and n are integers of 0-3; X is CR<1'>R<2'>, NR<1'>, O or S; R1 and R2 are respectively and independently hydrogen, alkyl, phenyl, 1naphthyl, 2naphthyl, alkoxy and ester substituted alkyl; R is hydrogen, alkyl, substituted phenyl, substituted alkyl, alkoxy, phenyl, 1-naphthyl, 2-naphthyl, halogen, cyano, carboxyl and hydroxyl; R2 is hydrogen, alkyl, phenyl, 1-naphthyl, 2-naphthyl or alkyl substituted phenyl; M' is P(O)(R3)2 or P(R3)2; R3 is alkyl, phenyl, 1-naphthyl, 2-naphthyl, substituted phenyl, furyl or thienyl; M isOTf, COOH or COOR5; OTf is trifluoromethanesulfonic acid group; and R5 is alkyl.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a chiral spirocyclic monophosphine-oxazoline ligand, an intermediate thereof and a preparation method thereof. Background technique [0002] Asymmetric catalytic reactions are research hotspots in the field of organic synthesis, and asymmetric catalytic hydrogenation reactions are research hotspots in the field of asymmetric catalytic synthesis. Asymmetric catalytic hydrogenation is one of the most favored asymmetric synthesis methods due to its perfect atom economy, cleanliness and high efficiency. [0003] In the early 1960s, people did not know whether the catalytic asymmetric hydrogenation reaction was feasible, and whether an excess of a certain enantiomer could be produced through the catalytic asymmetric reaction was confirmed by William S. Knowles. The experiment of William S.Knowles used the compound shown in the following formula A according to the structure published ...

AI Technical Summary

Problems solved by technology

[0018] In the field of asymmetric catalytic hydrogenation, although many chiral ligands and catalysts have been reported, overall, there are few catalyst systems applied to the asymmetric hydrogenation of unsaturated carboxylic compounds.

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