Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs.

Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs.
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DOI:
10.1021/ja9054959
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发表时间:
2009-08-26
影响因子:
15
通讯作者:
White MC
White MC
中科院分区:
化学1区
文献类型:
--
作者:
Rice GT;White MC

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报道了一种高选择性和通用性的钯/亚砜催化烯丙基C-H胺化反应合成顺式-1,3-氨基醇基序。在温和条件下实现这种反应性的关键是使用缺电子N-硝基苯氨基甲酸酯亲核试剂,其被认为通过原位提供更高浓度的阴离子物质来促进官能化。该反应被证明是正交的经典的C-C键形成/还原序列,以及基于氮烯的C-H胺化方法。
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.
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