Zinc promoted asymmetric propargylation of N-(2-chlorotetrafluoroethanesulfin)imines

•N-2-Chlorotetrafluoroethanesulfinamide was first used as chiral auxiliary in the propargylation of aldimines.•High diastereoselectivity was achieved under mild conditions.•A series of chiral propargylamines were synthesized.

Zinc promoted asymmetric Barbier-type homopropargylation of aldimines is demonstrated. 2-Chlorotetrafluoroethanesulfinamide was used as the chiral auxiliary and the corresponding homopropargylamines were obtained in good yields with up to 98% diastereoselectivity under mild conditions.

Graphical abstractZn-promoted propargylation of N-2-(chlorotetrafluoroethanesulfin)imines was achieved with good yields and high diastereoselectivities.Figure optionsDownload full-size imageDownload as PowerPoint slide