ja5b09773_si_002.cif (35.85 kB)
Asymmetric Synthesis of α‑Aminoboronic Acid Derivatives by Copper-Catalyzed Enantioselective Hydroamination
dataset
posted on 2015-12-23, 00:00 authored by Daiki Nishikawa, Koji Hirano, Masahiro MiuraA copper-catalyzed
regio- and enantioselective hydroamination
of alkenyl dan boronates (dan =1,8-diaminonaphthyl) with hydrosilanes
and hydroxylamines proceeds to deliver the chiral α-aminoboronic
acids in good yields with high enantiomeric ratios. The key to success
is the introduction of an umpolung, electrophilic amination strategy.
The copper catalysis can provide an unprecedented catalytic asymmetric
approach to alkyl-substituted chiral α-aminoboronic acid derivatives
of great potential in the fields of organic synthesis and medicinal
chemistry.
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Enantioselectiveumpolungcopper catalysisdiaminonaphthylenantiomeric ratioshydroxylamines proceedsyieldDerivativeHydroaminationAelectrophilic amination strategyacidhydroaminationalkenyl dan boronateshydrosilaneapproachAsymmetric SynthesisaminoboronicintroductionregioderivativechiralAminoboronicsynthesis