Ferrier-Petasis 重排 4-(乙烯氧基)氮杂环丁-2-酮：进入碳青霉烯和碳头孢烯的途径。

Ferrier-Petasis rearrangement of 4-(vinyloxy)azetidin-2-ones: an entry to carbapenams and carbacephams.

机构信息

Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

出版信息

J Org Chem. 2010 Oct 15;75(20):6990-3. doi: 10.1021/jo101463w.

PMID:20853897

Abstract

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.

摘要

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。