烯丙基叠氮环加成化学。光化学引发和碘化亚铜介导导致区域选择性提高。
Allenyl azide cycloaddition chemistry. photochemical initiation and CuI mediation leads to improved regioselectivity.
作者信息
Feldman Ken S, Hester D Keith, López Carlos Silva, Faza Olalla Nieto
机构信息
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA.
出版信息
Org Lett. 2008 Apr 17;10(8):1665-8. doi: 10.1021/ol800429j. Epub 2008 Mar 18.
Abstract
Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess CuI furnished functionalized 2,3-cyclopentenylindoles in good yield with only trace amounts of competitive C-N-bonded regioisomeric products. These results represent a significant departure from the modest-to-nonexistent regioselectivity that attended thermal cyclization of these allenyl azide substrates.
摘要
在过量碘化亚铜存在下，对2-(3-烯基)丙二烯基苯基叠氮化物进行辐照，以良好的产率得到了功能化的2,3-环戊烯基吲哚，仅生成痕量的竞争性C-N键合区域异构体产物。这些结果与这些丙二烯基叠氮化物底物热环化时适度至不存在的区域选择性形成了显著差异。
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