Developments in Nitrosocarbonyl Chemistry: Mild Oxidation of N-Substituted Hydroxylamines Leads to New Discoveries

Leoni I. Palmer; Charles P. Frazier; Javier Read de Alaniz

doi:10.1055/s-0033-1338569

Synthesis, Table of Contents

Synthesis 2014; 46(03): 269-280
DOI: 10.1055/s-0033-1338569

review

Developments in Nitrosocarbonyl Chemistry: Mild Oxidation of N-Substituted Hydroxylamines Leads to New Discoveries

Leoni I. Palmer

Department of Chemistry and Biochemistry, University of California-Santa Barbara, Santa Barbara, CA 93106-9510, USA Fax: +1(805)8934120 Email: javier@chem.ucsb.edu

,

Charles P. Frazier

Department of Chemistry and Biochemistry, University of California-Santa Barbara, Santa Barbara, CA 93106-9510, USA Fax: +1(805)8934120 Email: javier@chem.ucsb.edu

,

Javier Read de Alaniz*

Department of Chemistry and Biochemistry, University of California-Santa Barbara, Santa Barbara, CA 93106-9510, USA Fax: +1(805)8934120 Email: javier@chem.ucsb.edu

› Author Affiliations

Abstract

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Abstract

This account describes the discovery and development of mild and efficient protocols for the generation of highly reactive nitroso compounds to allow their subsequent use in previously inaccessible or challenging chemistries.

1 Introduction

2 Formation of Nitrosocarbonyl Compounds

3 The Nitrosocarbonyl Ene Reaction

3.1 Single-Pot Nitrosocarbonyl Ene Reactions

3.2 Copper-Catalyzed Aerobic Oxidation for the Nitrosocarbonyl Ene Reaction

4 The Hetero-Diels–Alder Reaction as a Platform for Studying Aerobic Oxidation

5 Dual Catalysis and α-Functionalization Reactions

5.1 α-Amination Reaction of β-Keto Esters

5.2 α-Oxygenation Reaction of β-Keto Esters

6 The Future of Nitroso Chemistry

Key words

aerobic oxidation - nitroso - α-functionalization - electrophilic synthon - hydroxylamines

Full Text

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