Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe, 658-8558, Japan.
Angew Chem Int Ed Engl. 2017 Dec 18;56(51):16342-16346. doi: 10.1002/anie.201708665. Epub 2017 Nov 27.
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.
本文提出了一种酰胺的反极性 α-芳基化新方法。通过 N-烷氧基酰胺原位生成的 O-硅基 N,O-氧代烯酮缩醛的亲核苯化，酰胺的α-碳原子上可以通过 N-O 键断裂，在两步一锅法中引入一个苯基。还描述了通过手性 N,O-氧代烯酮缩醛的非对映选择性芳基化来进行α-芳基酰胺的不对称合成。
