Asymmetric Three-Component Reaction of Two Diazo Compounds and Hyrdroxylamine Derivatives for the Access to Chiral α-Alkoxy-β-amino-carboxylates

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 alpha-alkoxy-beta-amino-carboxylate derivatives with two adjacent tertiary chiral centers in generally good yields and high to excellent enantioselectivity.