Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany.
Chemistry. 2010 Jan 18;16(3):956-63. doi: 10.1002/chem.200902472.
The substrate scope, the mechanistic aspects of the gold-catalyzed oxazole synthesis, and substrates with different aliphatic, aromatic, and functional groups in the side chain were investigated. Even molecules with several propargyl amide groups could easily be converted, delivering di- and trioxazoles with interesting optical properties. Furthermore, the scope of the gold(I)-catalyzed alkylidene synthesis was investigated. Further functionalizations of these isolable intermediates of the oxazole synthesis were developed and chelate ligands can be obtained. The use of Barluenga's reagent offers a new and mild access to the synthetically valuable iodoalkylideneoxazoles from propargylic amides, this reagent being superior to other sources of halogens.
研究了金催化唑合成的底物范围、反应机理以及具有不同脂肪族、芳香族和侧链官能团的底物。即使是具有多个炔丙酰胺基团的分子也可以很容易地转化，得到具有有趣光学性质的二氧杂和三唑。此外，还研究了金（I）催化亚烷基合成的范围。进一步开发了这些唑合成的可分离中间体的官能化，并获得了螯合配体。使用 Barluenga 试剂可以从炔丙酰胺中得到新的、温和的合成有价值的碘代亚烷基唑，该试剂优于其他卤素源。
