Azide-Enolate Cycloaddition-Rearrangement Enables Direct α-Amination of Amides and Enelactam Synthesis from Esters.

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Title

Azide-Enolate Cycloaddition-Rearrangement Enables Direct α-Amination of Amides and Enelactam Synthesis from Esters.

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The University of Auckland Library

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ResearchSpace@Auckland

Description

Azide-enolate cycloaddition-rearrangements offer potential for rapid access to diverse molecular frameworks, from simple precursors. We report here that investigations into the cycloadditions of ester or amide enolates with vinyl azides led to the identification of two reaction processes - direct α-amination of amides and lactams, and synthesis of ene-γ-lactams from esters. These reaction outcomes depended on the fate of key vinyl triazoline intermediates generated in the initial cycloadditio...

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Format

Research paper

Research format

Journal article

Date created

2023-02

Creator

Bell-Tyrer, Joseph J / Hume, Paul A / Grant, Phillip S / Brimble, Margaret A / Furkert, Daniel Plimmer

URL

https://hdl.handle.net/2292/63686

Related subjects

amination / azide-enolate cycloaddition / enelactam / reaction mechanisms / rearrangement / 03 Chemical Sciences

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