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Synthesis 2007(6): 795-818
DOI: 10.1055/s-2007-965963
DOI: 10.1055/s-2007-965963
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Synthesizing Allenes Today (1982-2006)
Further Information
Received
14 December 2006
Publication Date:
28 February 2007 (online)
Publication History
Publication Date:
28 February 2007 (online)
Abstract
Allenes have allowed chemists to access a variety of structurally interesting and biologically active products. The emergence of these unique compounds in organic synthesis is a direct result of the discovery and development of efficient protocols for their preparation. Moreover, efficient syntheses of the allenyl functionality are important to the synthetic community and will be reported and discussed in this review.
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1 Introduction
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2 Synthesis of Allenes with Aluminum Hydride Reagents
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2.1 Allenes from Propargyl Electrophiles
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2.2 Allenes from Enynes
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3 Allene Synthesis via Skeletal Rearrangement Reactions
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3.1 Allene Synthesis via Claisen Rearrangements
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3.2 Allene Synthesis via Other [3,3]-Sigmatropic Rearrangements
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3.3 Allene Synthesis via [2,3]-Sigmatropic Rearrangements
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3.4 Allenes via Carbene Rearrangement: The Doering-Moore-Skatteböl Reaction
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3.5 Allenes via Ene Reactions
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4 Allene Synthesis via Direct Homologation Reactions
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4.1 Wittig, Wittig-Horner, and Horner-Wadsworth-Emmons (HWE) Reactions
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4.2 Peterson Allenation
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4.3 Crabbé Homologation Reaction
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5 Allene Synthesis via β-Elimination Reactions
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5.1 β-Elimination of Enol Phosphates
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5.2 β-Elimination of Sulfoxide Derivatives
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5.3 Allenes via Deoxystannylation
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5.4 β-Elimination via Radical Intermediates
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5.5 Allenes from β-Chlorovinylsilanes
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5.6 Transition-Metal-Catalyzed β-Elimination
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6 Transition-Metal-Catalyzed Allene Synthesis
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6.1 Palladium-Catalyzed SN2′ Substitution of Dienes
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6.2 Palladium-Catalyzed 1,4-Addition of Enynes
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6.3 Palladium-Catalyzed Hydrogen Transfer Reactions of Propargyl Amines
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6.4 Palladium-Catalyzed Carbonylation Reaction of Propargyl Substrates
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6.5 Palladium-Catalyzed Cross-Coupling of Propargyl Derivatives
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6.6 Indium-Mediated Allene Formation
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6.7 Chromium-Catalyzed Allene Formation
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6.8 Ruthenium-Catalyzed Allene Formation
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6.9 Rhodium-Catalyzed Allene Formation
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6.10 A Zinc Carbenoid-Vinyl Copper Coupling to Form Allenes
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6.11 Titanium-Catalyzed Allene Formation
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6.12 Copper-Catalyzed Coupling of Allenyl Halides with Amide Derivatives
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7 Conclusion
Key words
allenes - rearrangements - homologation - elimination - additions
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