Catalytic asymmetric (4 + 1) annulation of nitroalkenes with allylic acetates: stereoselective synthesis of isoxazoline N-oxides12. Issue 29 (12th July 2019)

• Record Type: Journal Article
• Authors: Luo, Jinghua; Chen, Rongshun; Fan, Xia; Gong, Junyu; Han, Jie; He, Zhengjie
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 29(2019)
• Page Start: 6989
• Page End: 6993
• Publication Date: 2019-07-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01058k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A highly enantioselective catalytic asymmetric (4 + 1) annulation reaction of nitroalkenes and ammonium ylides is reported for the first time. Abstract : An asymmetric (4 + 1) annulation of α-nitro cinnamates with Morita–Baylis–Hillman (MBH) acetates catalyzed by α-isocupreine is reported. It provides chiral isoxazoline N -oxides in moderate to good yields with 88–99% ee, and represents the first catalytic asymmetric (4 + 1) annulation of activated nitroalkenes with in situ generated ammonium ylides. It also affords a practical and efficient access to chiral isoxazoline N -oxides.