PDF herunterladen
Synthesis 2009(4): 513-541  
DOI: 10.1055/s-0028-1083346
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Intermolecular Addition Reactions of N-Acyliminium Ions (Part II) [¹]

Arife Yazici, Stephen G. Pyne*
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia
Fax: +61(2)42214987; e-Mail: spyne@uow.edu.au;
Weitere Informationen

Publikationsverlauf

Received 22 September 2008
Publikationsdatum:
02. Februar 2009 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

This review highlights the advances in the literature up to July 2008 on the intermolecular reactions of acyclic and cyclic N-acyliminium ions. This is an update of an earlier review in 2000 on this topic and does not include intramolecular addition reactions to N-acyliminium ions which was recently reviewed. This review is presented in two parts, with the first part having dealt with acyclic and pyrrolidinone-based N-acyliminium ions. Part II continues with other five-membered heterocyclic derivatives and higher systems.

Part I

1 Introduction

2 Acyclic N-Acyliminium Ions

2.1 Synthesis of Acyclic N-Acyliminium Ion Precursors

2.2 Reactions of Acyclic N-Acyliminium Ions

2.2.1 Reactions with Nucleophiles

2.2.2 Cycloaddition Reactions

2.2.3 Cationic Carbohydroxylation Reactions

3 Cyclic N-Acyliminium Ions

3.1 Synthesis of Cyclic N-Acyliminium Ion Precursors

3.1.1 Preparation of Iminium Ions in situ by Anodic Oxidation

3.2 Five-Membered-Ring N-Acyliminium Ions

3.2.1 Reactions of Pyrrolidinone-Based N-Acyliminium Ions

Part II

3.2.2 Reactions of N-Acylpyrrolidine-Based N-Acyliminium Ions with Nucleophiles

3.2.2.1 Silicon-Based Nucleophiles

3.2.2.2 Aromatic Nucleophiles

3.2.2.3 Organostannanes

3.2.2.4 Organometallic Reagents

3.2.2.5 Carbonyl Compounds

3.2.2.6 Alkyl Radicals

3.2.2.7 Thiols

3.2.2.8 Active Methylene Compounds

3.2.3 Reactions of Oxazolidinone-Based N-Acyliminium Ions with Nucleophiles

3.2.3.1 Silicon-Based Nucleophiles

3.2.3.2 Organometallic Reagents

3.2.3.3 Active Methylene Compounds

3.2.4 Cyclocondensation Reaction of N-Aminidinyl Iminium Ions

3.3 Reactions of Six-Membered-Ring N-Acyliminium Ions

3.3.1 Reactions of Piperidinone-Based N-Acyliminium Ions with Nucleophiles

3.3.1.1 Silicon-Based Nucleophiles

3.3.1.2 Organostannanes

3.3.1.3 Organometallic Reagents

3.3.2 Reactions of N-Acylpiperidine-Based N-Acyliminium Ions

3.3.2.1 Reactions with Nucleophiles

3.3.2.2 Cycloaddition Reactions

3.3.3 Reactions of Piperazine-Based N-Acyliminium Ions with Nucleophiles

3.3.3.1 Silicon-Based Nucleophiles

3.3.3.2 Aromatic Nucleophiles

3.3.4 Reactions of Pyridine-Based N-Acyliminium Ions with Nucleophiles­

3.3.4.1 Organometallic Reagents

3.3.5 Reactions of N,O-Acetal Oxathiazinane N-Sulfonyl­iminium Ions with Nucleophiles

3.3.5.1 Organometallic Reagents

3.4 Reactions of Seven-Membered-Ring N-Acyliminium Ions

3.4.1 Reactions with Silicon-Based Nucleophiles

3.4.2 Cycloaddition Reactions

3.5 Reactions of Bicyclic N-Acyliminium Ions

3.5.1 Reactions with Nucleophiles

3.5.1.1 Silicon-Based Nucleophiles

3.5.1.2 Organometallic Reagents

3.5.1.3 Enamines

3.5.2 Cycloaddition Reactions

3.6 Other Systems

3.6.1 Silicon-Based Nucleophiles

4 Stereochemical Outcomes

5 Conclusions

Key words

N-acyliminium ion - nucleophilic addition - cycloaddition - aromatic electrophilic substitution - radical addition - peptides - pyrrolidines - piperidines