Tandem hetero diels-alder reaction: synthesis of oxygenated macrocycles.
[structure: see text]. C2-symmetric, oxygenated macrocycles have been synthesized from simple acyclic precursors in a single step by a tandem hetero Diels-Alder reaction. Thermolysis and Lewis acid catalysis can effect this novel transformation. The tandem reaction product is formed in preference to the intramolecular cycloaddition product, and an explanation for this result is proposed.
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, Irvine, California 92697-2025, USA.
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Bear
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Shea
D002384:Catalysis; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D018360:Crystallography, X-Ray; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D011714:Pyrans; D010100:Oxygen