(Thiolan-2-yl)diphenylmethyl benzyl ether/N,N′-diarylurea cocatalyzed asymmetric aziridination of cinnamyl bromide and aryl aldimine

Wang, Shang-Hua; Chein, Rong-Jie

(Thiolan-2-yl)diphenylmethyl benzyl ether/N,N′-diarylurea cocatalyzed asymmetric aziridination of cinnamyl bromide and aryl aldimine

2016

Wang, Shang-Hua | Chein, Rong-Jie

A dual catalyst system using THT-based chiral sulfide 2a and H-bond donor 10a was developed for the asymmetric imino Corey–Chaykovsky reaction. Under the optimum reaction conditions, cinnamyl bromide reacted with a wide scope of N-diphenylphosphinic aldimines, to give the major trans-aryl cinnamyl aziridines with up to 98% ee. The role of H-bond donor 10a was demonstrated empirically as well.

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