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Synlett
DOI: 10.1055/a-2538-2165
DOI: 10.1055/a-2538-2165
synpacts
Cyclic Imine-BF3 Complexes as Precursors for Functionalized Azacycles
Financial support from the National Institute of General Medical Sciences, National Institutes of Health (NIH-NIGMS) (R35GM149246) is gratefully acknowledged.
Abstract
Due to the relative instability and low electrophilicity of enolizable alicyclic imines, their functionalization commonly requires cryogenic temperatures and highly reactive nucleophiles such as organolithium compounds. Stable BF3 adducts of these imines streamline the synthesis of functionalized amines and obviate the need for cryogenic temperatures. In favorable cases, these adducts can be stored for over a year. The compatibility of cyclic imine-BF3 complexes with organometallic and radical-centered nucleophiles makes them ideal building blocks for functionalized azacycles.
1 Introduction
2 Synthesis of Cyclic Imine-BF3 Complexes
3 Reactions of Imine-BF3 Complexes with Organometallic Nucleophiles
4 Radical Additions to Imine-BF3 Complexes
5 Conclusions
Publication History
Received: 05 January 2025
Accepted after revision: 12 February 2025
Accepted Manuscript online:
12 February 2025
Article published online:
05 May 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
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