Journal
ORGANIC LETTERS
Volume 12, Issue 15, Pages 3540-3543Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol101375a
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Funding
- National Institutes of Health [CA042056]
- Skaggs Institute for Chemical Biology
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The first intramolecular cycloaddition reactions of cyclopropenone ketals with tethered electron-deficient, electron-rich, and neutral 1-substituted dienes are reported, constituting inverse electron demand, normal, and neutral Diels-Alder reactions, that provide exclusively the exo [4 + 2] cycloaddition products without the intervention of [1 + 2], [3 + 2], or [3 + 4] cycloadducts in reactions whose courses do not depend on the reaction conditions, the diene activating substituent, or the nature of the tethering.
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