Enantioselective aza-Henry reaction of t-Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts


SUSAM D. , TANYELİ C.

NEW JOURNAL OF CHEMISTRY, vol.41, no.9, pp.3555-3561, 2017 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 41 Issue: 9
  • Publication Date: 2017
  • Doi Number: 10.1039/c6nj04078k
  • Title of Journal : NEW JOURNAL OF CHEMISTRY
  • Page Numbers: pp.3555-3561

Abstract

An organocatalytic asymmetric aza-Henry reaction of t-Boc protected imines with nitroalkanes has been established by chiral acid-base type bifunctional Cinchona alkaloid/squaramide organocatalysts. The cooperation of a quinine motif as a base and sterically encumbered squaramide (H-bond donor) enabled mostly complete conversion of a range of reactants into the corresponding aza-Henry products at room temperature with good selectivities (up to 91% ee with 10 mol% catalyst loading).