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Organic Synthesis in Water pp 47–81Cite as

Hetero Diels-Alder reactions

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Abstract

Hetero Diels-Alder reactions have generally required activation of the requisite dienophile through substitution with electron-withdrawing substituents, Lewis-acid catalysis and/or the use of highly reactive dienes. These reactions, therefore, have traditionally been performed in aprotic organic solvents for the solubility and compatibility of the required reagents and catalysts. As a consequence, there are inherent limitations with respect to the scope and application of the hetero Diels-Alder reaction. Recently, the use of water as a solvent in hetero [4+2] cycloadditions has served both to complement existing methodology and to open up new reaction avenues for further synthetic exploitation. This chapter will highlight the developments over the past decade with respect to the use of water in heterocycloaddition [1] and related cycloreversion processes as well as applications in heterocyclic synthesis.

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© 1998 Thomson Science

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Parker, D.T. (1998). Hetero Diels-Alder reactions. In: Organic Synthesis in Water. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4950-1_2

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  • DOI: https://doi.org/10.1007/978-94-011-4950-1_2

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-0-7514-0410-4

  • Online ISBN: 978-94-011-4950-1

  • eBook Packages: Springer Book Archive

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