One-Pot Synthesis of α-Amino Acids through Carboxylation of Ammonium Ylides with CO2 Followed by Alkyl Migration
One-Pot Synthesis of α-Amino Acids through Carboxylation of Ammonium Ylides with CO2 Followed by Alkyl Migration
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DOI：
10.1021/acs.joc.6b00837
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发表时间：
2016-06-17
影响因子：
3.6
通讯作者：
Sato, Yoshihiro
中科院分区：
文献类型：
--
作者：
Mita, Tsuyoshi;Sugawara, Masumi;Sato, Yoshihiro
开发了一种使用二氧化碳 (CO2) 合成 α-氨基酸的简单而强大的方案。在烯丙基或苄基卤化物存在下，在 CO2 气氛 (1 atm) 下，α-氨基硅烷可以经历四个连续反应（形成铵盐、羧化、酯化和 2,3- 或 1,2-Stevens 重排）。值得注意的是，邻近氮原子位置的羧化是在温和条件下通过铵叶立德中间体进行的。
A simple, yet powerful protocol for alpha-amino acid synthesis using carbon dioxide (CO2) was developed. alpha-Amino silanes could undergo four successive reactions (formation of ammonium salt, carboxylation, esterification, and 2,3- or 1,2-Stevens rearrangement) in the presence of allylic or benzylic halides under a CO2 atmosphere (1 atm). It is noteworthy that carboxylation at the position adjacent to a nitrogen atom proceeded via an ammonium ylide intermediate under mild conditions.