Direct Synthesis of Unprotected 2-Azidoamines from Alkenes via an Iron-Catalyzed Difunctionalization Reaction
作者:Szabolcs Makai、Eric Falk、Bill Morandi
DOI:10.1021/jacs.0c11025
日期:2020.12.23
Unprotected, primary 2-azidoamines are versatile precursors to vicinal diamines, which are among the most common motifs in biologically active compounds. Herein, we report their operationally simple synthesis through an iron-catalyzed difunctionalization of alkenes. A wide array of alkene substrates are tolerated, including complex drug-like molecules and a tripeptide. Facile derivatizations of the
未受保护的初级 2-叠氮胺是邻二胺的通用前体,邻二胺是生物活性化合物中最常见的基序之一。在此,我们通过铁催化的烯烃双官能化报告了它们在操作上的简单合成。可以耐受多种烯烃底物,包括复杂的类药物分子和三肽。叠氮胺基团的轻松衍生证明了这种掩蔽二胺基序在化学选择性正交转化中的多功能性。该方法在 RO 20-1724 的简明合成以及 (±)-hamacanthin B 和 (±)-quinagolide 的正式全合成中的应用进一步证明了这种高官能团耐受反应的广泛合成潜力.