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Synthesis 1993; 1993(2): 165-178
DOI: 10.1055/s-1993-25823
review
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Alkoxyallenes - Building Blocks in Organic Synthesis

Reinhold Zimmer*
  • *Institut für Organische Chemie der Technischen Hochschule Darmstadt, Petersenstraße 22, D-6100 Darmstadt, Germany
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Publication History

Publication Date:
17 September 2002 (online)

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This review describes the preparation of alkoxyallenes and their reactions with organometallic reagents, nucleophilic and electrophilic compounds. Cycloaddition reactions of alkoxyallenes as 2π-components with electron-poor heterodienes lead to a variety of six-membered N,O-heterocycles (1,2-oxazines), tetrahydropyrans, and tetrahydropyridines, respectively. Syntheses of natural products or biologically interesting compounds by means of allenyl ethers as key intermediates are also reported. 1. Introduction 2. Deprotonation of Alkoxyallenes and Reactions with Electrophiles 3. Reactions with Organometallic Compounds 3.1. Cuprates and Copper Compounds 3.2. Zinc, Tin, and Titanium Compounds 4. Acidic Hydrolysis of Alkoxyallenes 5. Formation of 3-Alkoxydihydrofurans and Dihydro-3(2H)-furanones 6. Cycloaddition Reactions with Alkoxyallenes 6.1. Diels-Alder Reactions with Inverse Electron Demand 6.2. [3+2] Cycloaddition Reactions 7. Applications of Alkoxyallenes in Syntheses of Natural Products and Related Compounds 7.1. Formation of α-Methylene-γ-butyrolactone 119 7.2. Synthesis of Pyrenophorin 120 7.3. Synthesis of Lacrimin A 123 8. Miscellaneous Reactions 9. Conclusion

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