Inverse electron demand hetero-Diels–Alder reaction in preparing 1,4-benzodioxin from o-quinone and enamine |
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| Authors: | Jinsong Zhang Chris Taylor Erich Bowman Leo Savage-Low Michael W Lodewyk Larry Hanne Guang Wu |
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| Institution: | 1. Department of Chemistry and Biochemistry, California State University, Chico, CA 95929, United States;2. Department of Chemistry, University of California, Davis, CA 95616, United States;3. Department of Biological Sciences, California State University, Chico, CA 95929, United States;4. Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106, United States |
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| Abstract: | A process for synthesizing 1,4-benzodioxin, through oxidation of a phenol to an o-quinone followed by treatment with an enamine, has been developed. Adduct stereochemistry is found to be retained via this one-pot reaction. The method uses hypervalent iodine reagent under mild conditions and is compatible with a wide scope of phenols and enamines. |
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| Keywords: | o-Quinones Enamines 1 4-Benzodioxins Diels&ndash Alder reaction |
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