Allenes in Diels-Alder Cycloadditions
Date
2021
Authors
Hopf, Henning
Sherburn, Michael
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Georg Thieme Verlag
Abstract
For a long time, allenes-and cumulenic systems in general-played a relatively minor role in Diels-Alder cycloadditions. This situation has changed, since allenes are more readily available and as their unique stereochemical features in [4+2]cycloadditions are more widely recognized. This review presents a comprehensive overview of allenes in Diels-Alder processes using selected examples. Allenes in dienes, dienophiles and cycloadducts are covered, inter- and intramolecular Diels-Alder cycloadditions are discussed, and stereochemical features of the addition process are described. Areas of emerging importance are also covered, including allenic components in dehydro-Diels-Alder processes, and dendralenic allenes in Diels-Alder sequences for the rapid generation of target-relevant molecular complexity. Preparatively useful methods for allenic precursor synthesis are also discussed.
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Keywords
Diels–Alder addition, allenes as dienes and dienophiles, intermolecular cycloaddition, intramolecular cycloaddition, stereoselective synthesis, dehydro-Diels–Alder reactions, rapid generation of molecular complexity
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Synthesis
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Journal article
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Open Access
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Restricted until
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