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Hetero Diels-Alder Reactions of 1-Amino-3-siloxy-1,3-butadienes under Strictly Thermal Conditions

Yong Huang and Viresh H. Rawal

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

Y. Huang, V. H. Rawal, Org. Lett., 2000, 2, 3321-3323.

DOI: 10.1021/ol006404d (free Supporting Information)


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Abstract

The hetero Diels-Alder reaction of 1-amino-3-siloxy-1,3-butadiene with a range of unactivated carbonyl compounds and imines proceeds in good yields readily under remarkably mild conditions  at room temperature and in the absence of Lewis acid catalysts. The cycloadducts can be converted directly to the corresponding dihydro-4-pyrones and dihydro-4-pyridones.

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Key Words

Diels-Alder reaction, dihydro-4-pyrones


ID: J54-Y2000