Journal
HETEROCYCLES
Volume 84, Issue 2, Pages 843-878Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-11-S(P)65
Keywords
Gassman's Cationic [2+2] Cycloadditon; Vinyl Acetal Activation; Intramolecular [2+2] Cycloaddition; Cyclobutane Synthesis
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Funding
- ACS-PRF-AC
- The National Science Foundation [NSF] [CHE1012198]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1012198] Funding Source: National Science Foundation
- Grants-in-Aid for Scientific Research [23350020] Funding Source: KAKEN
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The development of an intramolecular variant of Gassman's cationic [2 + 2] cycloaddition is described herein. Mechanistic aspects of the stepwise nature of this cycloaddition process between vinyl acetals and unactivated olefins have been studied. We have also explored the scope of this reaction with regard to various oxygen-, nitrogen-, and carbon-tethered acetals to provide access to a diverse array of bicyclic scaffolds. Additionally, we have identified vinyl hemiaminals as having favorable reactivity for cationic [2 + 2] cycloaddition.
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