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Synlett 2010(7): 999-1026  
DOI: 10.1055/s-0029-1219790
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Recent Mechanistic Insights in the Singlet Oxygen Ene Reaction

Mariza N. Alberti, Michael Orfanopoulos*
Department of Chemistry, University of Crete, 71003 Voutes Campus, Heraklion, Crete, Greece
Fax: +30(2810)545001; e-Mail: orfanop@chemistry.uoc.gr;
Further Information

Publication History

Received 11 November 2009
Publication Date:
25 March 2010 (online)

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Abstract

Singlet oxygen reacts with alkenes, which bear allylic hydrogens, in an ene fashion to afford allylic hydroperoxides. This reaction, apart from its synthetic usefulness, has received extensive mechanistic attention. Numerous experimental studies (e.g., trapping of intermediates, deuterium kinetic isotope effects, regio- or stereoselectivity studies etc.) and to a lesser extend computational work, support a stepwise mechanism with the formation of a three-membered ring (perepoxide-like) intermediate. This Account mainly highlights our group’s earlier and recent experimental efforts to ascertain facts relating to this concept.

1 Introduction

2 Theoretical Calculations

3 Kinetic Isotope Effects

4 Regioselectivity

4.1 ‘cis Effect’ Selectivity

4.2 Anti ‘cis Effect’ Selectivity

4.3 The Large Group Nonbonding Effect

4.4 Geminal Selectivity with Respect to Allylic or Vinyl Substituent

4.5 Electron-Withdrawing Group at the α- and β-Position

4.6 Regioselective Self-Sensitized Oxygenation of Fullerene Derivatives

4.7 Solvent and Electronic Effects

4.7.1 Site Selectivity in the ¹O2 Ene Reaction of α,β-Unsaturated Esters and Acids

4.7.2 Site Selectivity in the ¹O2 Ene Reaction of Allylic Alcohols

4.7.3 Syn Selectivity of β,β-Dimethylstyrene

4.7.4 Site Selectivity of Isobutenylarenes

4.7.5 ‘Push-Pull’ Electronic Effect

5 Studies on Diastereoselectivity

5.1 Diastereoselectivity in Self-Sensitized Oxygenation of a Fullerene Derivative

5.2 Diastereoselectivity in the ¹O2 Ene Reaction of Chiral Functionalized Alkenes

6 Stereochemistry

7 Hypersensitive Probes in the ¹O2 Ene Reaction

8 The ¹O2 Ene Reaction in Confined Media

9 Concluding Remarks

Key words

singlet oxygen - ene reaction - kinetic isotope effect - ­selectivity studies - cyclopropyl probes

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