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

DOI

10.1021/acs.orglett.3c01396

Document Type

Journal Article

Publication Date

6-30-2023

Publication Title

Organic Letters

Volume

25

Issue

25

First Page

4638

Last Page

4643

ISSN

15237060

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.

Open Access

Hybrid_Gold

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