[reaction: see text] The enantioselective catalytic 1,4-addition to alpha,beta-unsaturated ketimines is an unprecedented process. Herein, we document the copper-catalyzed addition of dialkylzinc reagents to (2-pyridylsulfonyl)imines of chalcones. This process occurs rapidly in the presence of a chiral phosphoramidite ligand to afford exclusively the 1,4-addition product. In the case of addition of dimethylzinc, enantioselectivities in the range 70-80% ee are obtained. The presence of the metal-coordinating 2-pyridylsulfonyl group proved to be essential for this reaction to proceed.
![(S)-(+)-(3,5-Dioxa-4-phospha-cyclohepta[2,1-a3,4-a']dinaphthalen-4-yl)bis[(1S)-1-phenylethyl]amine Structure](https://image.chemsrc.com/caspic/174/380230-02-4.png)
![(11bS)-N,N-Bis[(R)-1-phenylethyl]-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine Structure](https://image.chemsrc.com/caspic/019/497883-22-4.png)