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Copper-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines
Zheng Ling1, Sonia Singh, Fang Xie
1School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China. xiefang@sjtu.edu.cn wanbin@sjtu.edu.cn.
Abstract:
A Cu-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines was developed, providing the corresponding chiral α-tertiary amines with up to 98% ee. The method tolerates some variations in cyclic N-sulfonyl ketimine and alkyne scope. These products could be used in several transformations, in particular, the products of 6-membered cyclic N-sulfonyl ketimines could be easily converted to linear chiral α-tertiary amines. This asymmetric alkynylation provides an efficient, gram-scale, low-cost transition-metal catalyzed synthesis of chiral α-tetrasubstituted propargylamines.