Asymmetric Three-Component Reaction of Two Diazo Compounds and Hyrdroxylamine Derivatives for the Access to Chiral α-Alkoxy-β-amino-carboxylates
Xiangji Yang, Kemiao Hong, Sujie Zhang, Zhijing Zhang, Su Zhou, Jingjing Huang, Xinfang Xu, Wenhao Hu
Abstract
Hydroxylamine derivatives are commonly used as both nitrogen and oxygen sources in the aminohydroxylation of alkenes, which is a powerful and practical method for the rapid assembly of synthetically useful 1,2-aminoalcohols. In this work, we disclose an unprecedented asymmetric formal aminohydroxylation of two diazo compounds with O-benzyl hydroxylamines, which involves a N–O bond activation, fragment modification, and reassembly cascade process. This cascade reaction forms multiple bonds in one-pot, including C═N, C–O, and C–C bonds, providing a potent complement for the aminohydroxylation using alkenes to that using two different diazo compounds, and leading to chiral α-alkoxy-β-amino-carboxylate derivatives with two adjacent tertiary chiral centers in generally good yields and high to excellent enantioselectivity.