Direct Imine Acylation: A Versatile Method for the Synthesis of 
Nitrogen-Containing Heterocycles, Spirocycles and Natural Products

William P. Unsworth; Richard J. K. Taylor

doi:10.1055/s-0035-1562095

Synlett, Table of Contents

Synlett 2016; 27(14): 2051-2064
DOI: 10.1055/s-0035-1562095

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Direct Imine Acylation: A Versatile Method for the Synthesis of Nitrogen-Containing Heterocycles, Spirocycles and Natural Products

Authors

William P. Unsworth*

Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK Email: william.unsworth@york.ac.uk Email: richard.taylor@york.ac.uk
Richard J. K. Taylor*

Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK Email: william.unsworth@york.ac.uk Email: richard.taylor@york.ac.uk

Abstract

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Abstract

Diverse nitrogen-containing heterocyclic compounds can be synthesised by the N-acylation of imines using functionalised carboxylic acids (Direct Imine Acylation, DIA). The carboxylic acids are activated in situ using the coupling agent propylphosphonic acid anhydride (T3P), before reacting with the imine coupling partner to generate N-acyliminium ions in situ, that can then be trapped by oxygen-, nitrogen-, sulfur- or carbon-based nucleophiles built into the carboxylic acid. This versatile, convergent method has been used to generate a wide range of products, including aromatic and aliphatic heterocycles, β-lactams, azaspirocycles and natural products.

1 Introduction

2 DIA in the Total Synthesis of ‘Upenamide

3 DIA with Benzoic Acid Derivatives

4 DIA with Aliphatic Carboxylic Acids

5 DIA in the Synthesis of β-Lactams

6 DIA in the Synthesis of Azaspirocycles

7 Mechanistic Studies

8 Conclusion

Key words

N-heterocycles - spirocycles - natural products - N-acyliminium ions - ‘upenamide - evodiamine - cavidine

Full Text

References

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