Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes

• DOI: 10.1021/acs.orglett.6b01299
• Publication Date: 2016-05-27T18:43:54Z
• Authors: Qing-Fa Zhou; Kui Zhang; Lingchao Cai; Ohyun Kwon
• Keywords: Nitronate; Furan

A novel and efficient phosphine-catalyzed intramolecular cyclization of α-nitroethylallenic esters is reported. This process appears to be practical for the stereoselective syntheses (Z)-furan-2(3H)-one oxime derivatives in excellent yields. Mechanistically, reaction involves a Michael addition an alkylideneazinate rearrangement cyclic nitronate α-nitrosodihydrofuran.