State Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University , Nanjing, 210009, P. R. China.
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
Org Lett. 2016 Jun 17;18(12):2954-7. doi: 10.1021/acs.orglett.6b01299. Epub 2016 May 27.
A novel and efficient phosphine-catalyzed intramolecular cyclization of α-nitroethylallenic 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 α-nitrosodihydrofuran.
报道了一种新型、高效的膦催化α-硝基烯丙基酯的分子内环化反应。该方法对于(Z)-呋喃-2(3H)-酮肟衍生物的立体选择性合成具有较好的应用价值,能以优异的收率得到目标产物。反应经历了膦催化的亚烷基偶氮化物的迈克尔加成和环状硝代醇的重排过程,生成了α-硝基二氢呋喃。