2-Methylquinoline → 2-Methyl-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

In 60 ml of methylene chloride, 1.00 g of 2-methylquinoline was dissolved, and as a catalyst, 6.7 mg (0.2 mol %) of a crystalline (R)-chloro[(1,2,3,4,5-η)-pentamethyl-2,4-cyclopentadien-1-yl](2-pyrrolidinecarboxamidato-κN1, κN2)iridium(III) complex (Cp*Ir(Cl−)(R-PA-H+)) was added. After cooling to −10° C., 8.4 ml of a mixed solvent of formic acid/triethylamine (molar ratio: 5/2) was added dropwise, and the mixture was stirred at the same temperature for 2 days to give 2-methyl-1,2,3,4-tetrahydroquinoline (degree of conversion: 73%). The R-enantiomer was in excess and the optical purity was 90.2% ee.

Provenance & Evidence