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Synthesis 2004(2): 161-201
DOI: 10.1055/s-2004-815914
DOI: 10.1055/s-2004-815914
REVIEW
© Georg Thieme Verlag Stuttgart · New York
β-Oxidation of α,β-Unsaturated Carbonyl Compounds
Further Information
Received
10 July 2003
Publication Date:
13 January 2004 (online)
Publication History
Publication Date:
13 January 2004 (online)
Abstract
The replacement of a β-hydrogen on an α,β-unsaturated carbonyl system with a non-hydrogen, non-carbon atom amounts to either a net two electron oxidation or an isohypsic substitution at the β-carbon. The resulting compounds are the functional equivalents of β-dicarbonyl derivatives. Although many methods have been developed to effect this transformation, they lack generality and the process remains an underutilized one in organic synthesis.
1 Introduction
1.1 Scope
1.2 Organization
1.3 General Strategies
2 Oxygen
2.1 Direct Oxidation
2.2 Addition-Oxidation
2.3 Epoxide Rearrangement
2.3.1 Acid Catalyzed, Base Catalyzed, Thermal Isomerizations
2.3.2 Photolytic Isomerization
2.3.3 Enzymatic Isomerization
2.3.4 Palladium Catalyzed (Noyori) Rearrangement
2.3.5 Eschenmoser Fragmentation and Related Reactions
2.4 Oxidation of Aldols and Acetaldols
2.5 Addition-Elimination
2.6 Selenium Mediated Reactions
2.7 Isohypsic Rearrangement
2.8 Other Oxidations
3 Nitrogen
3.1 Direct Amination
3.2 Addition-Oxidation
3.3 Addition-Elimination
3.4 Reductive Addition
3.5 Isoxazoles
3.6 Nitration
3.7 Azides
3.8 Ene-Isomerization
3.9 Aziridine and Azide Rearrangement
4 Sulfur
4.1 Episulfides (Thiiranes) or Episulfoniums
4.2 Addition-Oxidation
4.3 Addition-Elimination
4.4 Metalation-Sulfenylation
4.5 Oxidative Addition-Elimination
4.6 Isohypsic Rearrangement
5 Halogen
5.1 Oxidative Addition-Elimination
5.2 Addition-Oxidation
5.3 Umpolung-Halogenation
6 Phosphorus
7 Silicon
7.1 Direct Silylation
7.2 Metalation-Silylation
8 Metals
8.1 Direct Metalation
9 Carbon
10 Other Elements
11 Heteroatom Exchange
12 Conclusion
Key words
conjugation - Michael additions - oxidations - Wacker reactions - organometallic reagents
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Sommer, T. J. unpublished results.
265See ref. 37.