(Thiolan-2-yl)diphenylmethyl benzyl ether/N, N′-diarylurea cocatalyzed asymmetric aziridination of cinnamyl bromide and aryl aldimine. Issue 21 (26th May 2016)

• Record Type: Journal Article
• Authors: Wang, Shang-Hua; Chein, Rong-Jie
• Is Part Of: Tetrahedron. Volume 72:Issue 21(2016)
• Page Start: 2607
• Page End: 2615
• Publication Date: 2016-05-26
• Subjects: Chiral sulfide -- Sulfur ylide -- Asymmetric aziridination -- Corey–Chaykovsky -- H-bind donor; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2014.12.063
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A dual catalyst system using THT-based chiral sulfide2a and H-bond donor10a 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 donor10a was demonstrated empirically as well. Graphical abstract: