The Diels−Alder Reactions of Quinone Imine Ketals:  A Versatile Synthesis of Highly Substituted 5-Methoxyindoles

The Diels−Alder Reactions of Quinone Imine Ketals:  A Versatile Synthesis of Highly Substituted 5-Methoxyindoles

N-Benzoylated quinone imine ketals undergo smooth cycloadditions in a [4 + 2] sense to yield the expected cycloadducts. The crude cycloadducts, when subjected to a short series of simple transformations, produce synthetically useful quantities of 5-methoxyindoles in excellent overall yields.

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Veröffentlicht in:Organic letters 2001-10, Vol.3 (21), p.3325-3327
Hauptverfasser: Banfield, Scott C, England, Dylan B, Kerr, Michael A
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Benzoquinones - chemistry
Chemistry, Pharmaceutical
Imines - chemistry
Indoles - chemical synthesis
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Zusammenfassung:N-Benzoylated quinone imine ketals undergo smooth cycloadditions in a [4 + 2] sense to yield the expected cycloadducts. The crude cycloadducts, when subjected to a short series of simple transformations, produce synthetically useful quantities of 5-methoxyindoles in excellent overall yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016562k