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

Abstract

This review highlights the advances in the literature up to July2008 on the intermolecular reactions of acyclic and cyclic N-acyliminium ions. This is an updateof an earlier review in 2000 on this topic and does not includeintramolecular addition reactions to N-acyliminiumions which was recently reviewed. This review is presented in twoparts, with the first part having dealt with acyclic and pyrrolidinone-based N-acyliminium ions. Part II continueswith other five-membered heterocyclic derivatives and higher systems. Part I 1 Introduction 2 Acyclic N-Acyliminium Ions 2.1 Synthesis of Acyclic N-AcyliminiumIon Precursors 2.2 Reactions of Acyclic N-AcyliminiumIons 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-AcyliminiumIon Precursors 3.1.1 Preparation of Iminium Ions in situ by Anodic Oxidation 3.2 Five-Membered-Ring N-AcyliminiumIons 3.2.1 Reactions of Pyrrolidinone-Based N-AcyliminiumIons 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-AcyliminiumIons 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-AminidinylIminium Ions 3.3 Reactions of Six-Membered-Ring N-AcyliminiumIons 3.3.1 Reactions of Piperidinone-Based N-AcyliminiumIons 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-AcyliminiumIons with Nucleophiles 3.3.3.1 Silicon-Based Nucleophiles 3.3.3.2 Aromatic Nucleophiles 3.3.4 Reactions of Pyridine-Based N-AcyliminiumIons with Nucleophiles- 3.3.4.1 Organometallic Reagents 3.3.5 Reactions of N, O-Acetal Oxathiazinane N-Sulfonyl-iminiumIons with Nucleophiles 3.3.5.1 Organometallic Reagents 3.4 Reactions of Seven-Membered-Ring N-AcyliminiumIons 3.4.1 Reactions with Silicon-Based Nucleophiles 3.4.2 Cycloaddition Reactions 3.5 Reactions of Bicyclic N-AcyliminiumIons 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