Catalytic Oxyamidation of Indoles
Catalytic Oxyamidation of Indoles
复制标题
DOI：
10.1002/anie.200906650
复制
发表时间：
2010-01-01
影响因子：
16.6
通讯作者：
Dauban, Philippe
中科院分区：
文献类型：
--
作者：
Beaumont, Stephane;Pons, Valerie;Dauban, Philippe
自从Baeyer在1866年首次制备吲哚以来，[1]由于其在许多生物活性天然产物（包括一些有用的药物）的结构中的普遍存在，其化学已经被广泛研究。[1，2]吲哚化学仍然是一个非常感兴趣的领域，正如最近几篇致力于该领域的评论所证明的那样。[3]特别是，许多注意力都集中在C2和C3位置的氧化功能化方法的开发上，[4]这是Witkop开创的领域，[1c]因为这些氧化可以提供快速路线，以获得含有吲哚框架的新天然产物，如chaetominine（1）[5]和psychotrimine（2）。[6]烯烃的催化氧化双官能化为各种重要的支架提供了直接途径，如邻二胺和氨基醇。虽然已经描述了使用钯（II）化学的有效程序，[7]催化氮烯转移提供了一个可能的替代方案。后者通常提供C2 H4-胺化或烯烃氮丙啶化产物，[8]但最近的研究表明，在葡萄糖醛[9]和吲哚的情况下可以实现正式烯烃氧酰胺化。[10]这些氮烯转移已经通过将酰基氮烯或氨磺酰基氮烯栓系到基底上而成功地开发，从而确保分子内转移的效率和完全的区域选择性。
Since the first preparation of indole by Baeyer in 1866,[1] its chemistry has been extensively investigated as a consequence of its prevalence in the structures of many biologically active natural products, including some useful drugs.[1, 2] Indole chemistry still remains an area of great interest as demonstrated by several recent reviews dedicated to this field.[3] In particular, much attention has been focused towards the development of methodologies for oxidative functionalization at the C2 and C3 positions,[4] a field pioneered by Witkop,[1c] since these oxidations can provide rapid routes to new natural products that contain an indole framework, such as chaetominine (1)[5] and psychotrimine (2).[6]The catalytic oxidative difunctionalization of alkenes offers a direct route to various important scaffolds, such as vicinal diamines and aminoalcohols. Although efficient procedures have been described using palladium (II) chemistry,[7] catalytic nitrene transfers offer a possible alternative. The latter generally afford CÀH-aminated or olefin aziridination products,[8] but recent studies have demonstrated that formal alkene oxyamidation can be achieved in the case of glucals [9] and indoles.[10] These nitrene transfers have been successfully developed by tethering an acylnitrene or a sulfamoylnitrene onto the substrate, thereby ensuring efficiency and complete regioselectivity for the intramolecular