Nucleophilic Arylation of N,O-Ketene Acetals with Triaryl Aluminum Reagents: Access to α-Aryl Amides through an Umpolung Process
Nucleophilic Arylation of N,O-Ketene Acetals with Triaryl Aluminum Reagents: Access to α-Aryl Amides through an Umpolung Process
复制标题
N,O-乙烯酮缩醛与三芳基铝试剂的亲核芳基化：通过 Umpolung 过程获得 α-芳基酰胺
DOI：
10.1002/anie.201708665
复制
发表时间：
2017
期刊：
影响因子：
--
通讯作者：
Miyata Okiko
中科院分区：
文献类型：
--
作者：
Takeda Norihiko;Futaki Erika;Kobori Yukiko;Ueda Masafumi;Miyata Okiko
提出了一种酰胺类化合物的α-芳基化反应的新方法。通过由N-烷氧基酰胺原位生成的O-甲硅烷基N，O-烯酮缩醛的亲核苯基化，可以在两步一锅法中通过N-O键断裂将苯基引入到酰胺的α-碳原子上。还描述了通过手性N，O-烯酮缩醛的非对映选择性芳基化反应不对称合成α-芳基酰胺。
A novel approach for the umpolung α‐arylation of amides is presented. By the nucleophilic phenylation of O‐silyl N,O‐ketene acetals, generated in situ from N‐alkoxy amides, a phenyl group can be introduced onto the α‐carbon atom of amides through N−O bond cleavage in a two‐step, one‐pot process. The asymmetric synthesis of α‐aryl amides through the diastereoselective arylation of a chiral N,O‐ketene acetal is also described.