Institute of Microbial Chemistry (BIKAKEN) Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan).
JST, ACT-C, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan).
Angew Chem Int Ed Engl. 2015 May 18;54(21):6236-40. doi: 10.1002/anie.201501607. Epub 2015 Mar 30.
A direct aldol reaction of an α-azido 7-azaindolinylamide, promoted by a Cu-based cooperative catalyst, is documented. Aromatic aldehydes bearing an ortho substituent exhibited diastereodivergency depending on the nature of the chiral ligands used. Smooth reactions with ynals highlighted the broad substrate scope. A vicinal azido alcohol unit in the product allowed direct access to the corresponding aziridine and facile hydrolysis of the 7-azaindolinylamide moiety furnished enantioenriched β-hydroxy-α-azido carboxylic acid derivatives.
本文报道了一种由 Cu 基协同催化剂促进的α-叠氮基 7-氮杂吲哚酰胺的直接羟醛反应。带有邻位取代基的芳醛根据所使用的手性配体的性质表现出非对映选择性。与 ynals 的顺利反应突出了广泛的底物范围。产物中相邻的叠氮醇单元允许直接得到相应的氮杂环丙烷，并且 7-氮杂吲哚酰胺部分的易于水解可得到对映体富集的β-羟基-α-叠氮羧酸衍生物。
