用于制备顺式-1,3-氨基醇基序的烯丙基C-H胺化反应。
Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs.
作者信息
Rice Grant T, White M Christina
机构信息
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
出版信息
J Am Chem Soc. 2009 Aug 26;131(33):11707-11. doi: 10.1021/ja9054959.
Abstract
A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.
摘要
报道了一种高度选择性且通用的钯/亚砜催化的烯丙基C-H胺化反应，该反应可用于合成顺式1,3-氨基醇结构单元。在温和条件下实现这种反应活性的关键在于使用缺电子的N-硝酰基氨基甲酸酯亲核试剂，据认为这些亲核试剂通过原位提供更高浓度的阴离子物种来促进官能化。该反应被证明与经典的C-C键形成/还原序列以及基于氮宾的C-H胺化方法相互正交。
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