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