Nucleophilic Addition to C=O and C=N Bonds by Nucleophiles Containing a Diazo Group

Abstract

This account summarizes recent developments in the ­nucleophilic addition reaction of diazo compound derived anion or enolate with electrophilic C=O and C=N bonds. Subsequent ­reaction of the addition products under transition-metal-catalyzed conditions, as well as their synthetic utility, are also presented.

1 Introduction

2 Reaction with Diazo Acylmethane Derived Anion

2.1 C=O Bond Addition

2.2 C=N Bond Addition

3 Reaction with α-Diazo β-Ketoester Derived Enolate

3.1 C=O Bond Addition

3.2 C=N Bond Addition

4 Subsequent Transformations of the Addition Products

4.1 Transition-Metal-Catalyzed Reaction: 1,2-Migration

4.2 Substitution in the β-Position and Subsequent Reactions

4.3 Oxidation/Reduction: Stereoselective Approach to
α,β-Dihydroxy Esters and α-Dihydroxy β-Amino Esters

5 Conclusions and Prospects

Key words

nucleophilic addition - diazo carbonyl compounds - ­anion - enolate - aldehyde - ketone - imine

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