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

作者:Zhou Qing Fa; Zhang Kui; Cai Lingchao; Kwon Ohyun*
来源:Organic Letters, 2016, 18(12): 2954-2957.
DOI:10.1021/acs.orglett6b01299

摘要

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