Enantioselective synthesis of chiral cyclic hydroxylamine ethers via NiH-catalyzed cyclization of alkyne-oxime ethers

As important scaffolds in organic synthesis, chiral hydroxylamines are highly sought after. Reported herein is the first NiH-catalyzed asymmetric addition to oxime ethers, affording cyclic allylic hydroxylamine ethers with good yields and excellent enantioselectivity. This method offers a general route for the conversion of readily available oxime ethers to chiral hydroxylamine ether derivatives, while also establishing a novel approach to alkyne hydrofunctionalization.