Photoredox α-vinylation of α-amino acids and N-aryl amines.

Photoredox α-vinylation of α-amino acids and N-aryl amines.
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DOI:
10.1021/ja506094d
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发表时间:
2014-08-20
影响因子:
15
通讯作者:
MacMillan DW
MacMillan DW
中科院分区:
化学1区
文献类型:
--
作者:
Noble A;MacMillan DW

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开发了一种新的偶联方案,允许乙烯基砜与光氧化还原生成的α-氨基结合来提供广泛多样性的烯丙基胺。N-芳基叔胺的直接C-H乙烯基化,以及N-Bocα-氨基酸的脱羧基乙烯基化,以高产率和出色的烯烃几何控制进行。这种新的烯丙胺形成反应的用途已经通过几个天然产物和一些已建立的药效团的合成得到了证明。
A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C–H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.
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