Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, USA.
Chem Soc Rev. 2014 Aug 7;43(15):5151-62. doi: 10.1039/c4cs00072b.
Metal-stabilized carbenes derived from diazo compounds have become broadly useful reactive intermediates for organic synthesis. This tutorial review will describe the recent advances in using N-sulfonyl-1,2,3-triazoles as precursors for the formation of metal-bound imino carbene intermediates. These intermediates undergo a variety of synthetically useful transformations, which include transannulation reactions to generate new heterocycles, cyclopropanation and subsequent ring expansions, ylide formation with subsequent rearrangements, and C-H functionalization. Furthermore, many of these transformations can be conducted with high levels of enantioselectivity by use of chiral rhodium(II) catalysts.
金属稳定的卡宾衍生自重氮化合物，已经成为有机合成中广泛应用的反应性中间体。本综述将描述使用 N-磺酰基-1,2,3-三唑作为前体形成金属键合亚氨基卡宾中间体的最新进展。这些中间体经历了多种具有合成用途的转化，包括转环反应生成新的杂环、环丙烷化和随后的环扩张、叶立德形成和随后的重排，以及 C-H 官能化。此外，许多这些转化可以通过使用手性铑(II)催化剂实现高水平的对映选择性。
