通过导向氨化合成不对称偕二胺。
Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination.
机构信息
Department of Chemistry, University of Texas at Austin, 105 E 24th St., Austin, Texas 78712, United States.
Department of Chemistry, University of Illinois Urbana-Champaign, 600 S. Mathews, Urbana, Illinois 61812, United States.
出版信息
Org Lett. 2022 Aug 5;24(30):5513-5518. doi: 10.1021/acs.orglett.2c01911. Epub 2022 Jul 21.
Abstract
Vicinal diamines are a common motif found in biologically active molecules. The hydroamination of allyl amine derivatives is a powerful approach for the synthesis of substituted 1,2-diamines. Herein, the rhodium-catalyzed hydroamination of primary and secondary allylic amines using diverse amine nucleophiles, including primary, secondary, acyclic, and cyclic aliphatic amines to access a wide range of unsymmetrical vicinal diamines, is presented. The utility of this methodology is further demonstrated through the rapid synthesis of several bioactive molecules and analogs.
摘要
邻二胺是生物活性分子中常见的结构基序。烯丙基胺衍生物的氨氢化反应是合成取代的 1,2-二胺的有效方法。在此，展示了使用各种胺亲核试剂（包括伯胺、仲胺、无环和环状脂肪族胺）进行伯和仲烯丙基胺的铑催化氨氢化反应，以获得广泛的不对称邻二胺。该方法的实用性通过几种生物活性分子和类似物的快速合成得到了进一步证明。
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