Kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and its structural analogs by using 2-arylpropionyl chlorides

摘要

Acylation of 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with the acyl chlorides of naproxen, ibuprofen, and 2-phenylpropionic acid has been found to lead to efficient kinetic resolution with predominant formation of the (S,S)-(R,R)-diastereoisomers. The highest acylation stereoselectivity was found in toluene at-20°C. No significant kinetic resolution of N-(sec-butyl)aniline and 2-methylpiperidine was achieved by using 2-arylpropionyl chlorides.