钯极化氮杂邻二甲苯的不对称环加成反应
Asymmetric cycloadditions of palladium-polarized aza-o-xylylenes.
作者信息
Wang Chao, Tunge Jon A
机构信息
Department of Chemistry, University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
出版信息
J Am Chem Soc. 2008 Jul 2;130(26):8118-9. doi: 10.1021/ja801742h. Epub 2008 Jun 6.
Abstract
Vinyl benzoxazinanones undergo highly enantioselective decarboxylative cycloadditions with electron-deficient olefins in the presence of palladium catalysts. Palladium induces the decarboxylation of the parent benzoxazinanones under mild conditions to produce an intermediate that can be described as a polarized aza-o-xylylene. These intermediates undergo a formal [4 + 2] cycloaddition with good Michael acceptors to produce highly substituted hydroquinolines with excellent regio-, diastereo-, and enantioselectivities.
摘要
乙烯基苯并恶嗪酮在钯催化剂存在下与缺电子烯烃发生高度对映选择性脱羧环加成反应。钯在温和条件下诱导母体苯并恶嗪酮脱羧，生成一种可描述为极化氮杂邻二甲苯的中间体。这些中间体与良好的迈克尔受体进行形式上的[4 + 2]环加成反应，以优异的区域选择性、非对映选择性和对映选择性生成高度取代的氢喹啉。
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