Ambident Reactivity of Nitroso Compounds for Direct Amination and Hydroxylation of Carbonyls

To Professor Herbert Mayr on the occasion of his 70th birthday

Abstract

Functionalization of carbonyls, particularly with a heteroatom subunit, is an important synthetic transformation. Utilization of ambident electrophiles for such a strategy is advantageous because two different heteroatom units can be installed from a single source under judicial reaction conditions. Recently, there have been increased examples for the construction of C–O and C–N bonds using nitroso compounds, a prototype of ambident electrophiles. In this short review, we discuss the advantages and challenges of exploiting nitroso compounds in organic synthesis with specific focus on nitroso aldol type processes for the direct hydroxylation and amination of carbonyl compounds.

1 Introduction

2 Prime Challenges in Nitroso Aldol Reactions

3 Direct Hydroxylation Reactions

4 Direct Amination Reactions

5 Conclusion and Outlook

Key words

nitroso compounds - hydroxylation - amination - oxidation - N–O bond cleavage

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