Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
J Org Chem. 2010 Oct 15;75(20):6990-3. doi: 10.1021/jo101463w.
Trimethylsilyl triflate promotes Ferrier-Petasis rearrangement of 4-(vinyloxy)-, 4-(propenyloxy)-, and 4-(isopropenyloxy)azetidin-2-ones to corresponding 4-(carbonylmethyl)azetidin-2-ones. The latter compounds may serve as attractive intermediates in the synthesis of carbapenem antibiotics. To illustrate the potential of this reaction, selected rearrangement products have been transformed into carbapenams.
三甲基硅基三氟甲磺酸酯促进 4-(乙烯氧基)-、4-(丙烯氧基)-和 4-(异丙烯氧基)氮杂环丁-2-酮的费里耶-佩塔西重排反应，生成相应的 4-(羰基甲基)氮杂环丁-2-酮。后一种化合物可用作合成碳青霉烯类抗生素的有吸引力的中间体。为了说明该反应的潜力，选择的重排产物已转化为碳青霉胺。
