保护团

烯丙氧基羰基保护基 Alloc Protecting Group

概要

烯丙氧基羰基保护基(allyloxycarbonyl, Alloc)、经常用于通过形成氨基甲酸酯形成来保护胺基。
该保护基在强碱性条件下的酯的水解条件・亲核条件・比较弱的质子还原条件下都能显示出比较强的稳定性,通常使用Pd(0)催化的亲核取代反应进行脱保护。


基本文献

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反应机理

保护

烯丙基氯甲酸酯(Alloc-Cl)常用作反应试剂。加入吡啶或三乙胺作为碱并与胺反应。对于氨基酸的保护等,使用无机碱的Schotten-Baumann条件也很常见。

脱保护

在Pd(0)催化剂作用下、生成π-烯丙基钯中间体、当适当的亲核试剂(如吗啉或1,3-二酮)共存时,脱保护可以以这样的方式进行。脱保护的胺亲核攻击π-烯丙基钯,并得到N-烯丙胺作为副产物。

反应实例

I2条件下的脱保护[1]

参考文献

  1. Szumigala, R. H. Jr.; Onofiok, K.; Karady, S.; Armstrong, J. D. III; Miller, R. A.Tetrahedron Lett. 2005, 46, 4403. doi: 10.1016/j.tetlet.2005.04.064

关联书籍(日亚价格)

Greene's Protective Groups in Organic Synthesis

Greene’s Protective Groups in Organic Synthesis

  • 著者Peter G. M. Wuts
  • 参考価格¥ 12,094日元
    価格¥ 11,813(2018/07/08 10:25時点)
  • 出版社John Wiley & Sons Inc

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LuWenjie

LuWenjie

京都大学药学博士,现某化学企业小职员,化学空间员工副代表,网页小编&翻译。

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