Diastereoselective addition of functionalized organolithium compounds to (-)-menthone - synthesis of chiral ligands for enantioselective addition of diethylzinc to aldehydes

The addition of N-and S-functionalized organolithium compounds to (-)-menthone was studied and a series of new chiral substituted neomenthol derivatives has been isolated. The new chiral compounds have been applied as precatalysts for addition of diethylzinc to aldehydes and enantioselectivity of up to 80% ee was achieved.