Recent Advances on Asymmetric Nitroso Aldol Reaction

Dedicated to Professor Carmen Nájera, the 2015 recipient of the IUPAC 2015 Distinguished Women in Chemistry or Chemical Engineering Award

Abstract

The reaction of aromatic nitroso derivatives with enolizable carbonyl compounds (nitroso aldol reaction) to give either α-hydroxyamino or α-aminoxy carbonyl compounds is an important synthetic method. This review illustrates the recent advances in rendering the process regio- and enantioselective as well as catalytic. By employing metal and organic catalysts a range of α-amino (α-oxyamination) and α-hydroxy (α-aminoxylation) carbonyl derivatives can be generated with total regioselectivity and high levels of enantiomeric excess.

1 Introduction

2 Metal-Catalyzed Reactions

3 Organocatalyzed Reactions

4 Enamine Metal-Free Reactions

5 Concluding Remarks

Key words

asymmetric nitroso aldol - aminoxylation - hydroxyamination - α-hydroxy carbonyls - α-amino carbonyls - chiral Lewis acids - organocatalysts

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