[3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines

Org Lett. 2023 Jun 30;25(25):4638-4643. doi: 10.1021/acs.orglett.3c01396. Epub 2023 Jun 15.

Abstract

We have developed a one-pot synthetic method for producing 1,2-diamines from easily prepared and commercially available precursors through a formal umpolung process. Our method utilizes an efficient [3 + 2] cycloaddition as the key step in forming substituted 1,2-diamines in moderate to high yields. These resulting compounds can undergo subsequent transformations, demonstrating their utility as synthetic building blocks for more complex scaffolds. Finally, we propose a reasonable mechanism for this transformation using density functional theory modeling, justifying the experimental observations.

MeSH terms

  • Amines
  • Cycloaddition Reaction
  • Diamines*
  • Imines
  • Oxides*

Substances

  • Diamines
  • Oxides
  • Imines
  • Amines