Canterbury Daniel P, Herrick Ildiko R, Um Joann, Houk K N, Frontier Alison J
Department of Chemistry, University of Rochester, Rochester, New York, 14627.
Tetrahedron. 2009 Apr 18;65(16):3165-3179. doi: 10.1016/j.tet.2008.10.003.
A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described. The [3+2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives an isolable isoxazoline intermediate, which upon oxidation undergoes stereoselective extrusion of nitrosomethane to give aryl vinyl or divinyl ketones.
描述了一种用于合成纳扎罗夫环化底物的温和、简便的反应序列。硝酮与缺电子炔烃的[3+2]偶极环加成反应生成一种可分离的异恶唑啉中间体，该中间体经氧化后发生立体选择性的亚硝基甲烷消除反应，生成芳基乙烯基或二乙烯基酮。
