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Diels-Alder Reactions of 1-Alkoxy-1-amino-1,3-butadienes: Direct Synthesis of 6-Substituted and 6,6-Disubstituted 2-Cyclohexenones and 6-Substituted 5,6-Dihydropyran-2-ones

Pavel K. Elkin, Nathaniel D. Durfee and Viresh H. Rawal*

*Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, United States, Email:

P. K. Elkin, N. D. Durfee, V. H. Rawal, Org. Lett., 2021, 23, 5288-5293.

DOI: 10.1021/acs.orglett.1c01031

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1-Alkoxy-1-amino-1,3-butadienes undergo Diels-Alder (DA) and hetero-Diels-Alder (HDA) reactions under mild reaction conditions with a variety of electron-deficient dienophiles. The hydrolysis of the DA cycloadducts provides 6-substituted and 6,6-disubstituted 2-cylohexenones in good yields with excellent regioselectivities, whereas HDA cycloadducts afford 6-substituted 5,6-dihydropyran-2-ones.

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Key Words

Diels-Alder reaction, 5,6-dihydropyran-2-ones

ID: J54-Y2021