Rapid Syntheses of Benzopyrans from o-OBOC Salicylaldehydes and Salicyl alcohols: A Three-Component Reaction

The Diels−Alder reactions of o-quinone methides generated from OBOC-salicylic aldehydes and alcohols are described, allowing for the synthesis of various substituted benzopyrans. The low temperatures employed for this procedure enable high diastereoselectivity in reactions with β-substituted o-quino...

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Veröffentlicht in:	Journal of organic chemistry 2002-10, Vol.67 (20), p.6911-6915
Hauptverfasser:	Jones, Ryan M, Selenski, Carolyn, Pettus, Thomas R. R
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Benzopyrans - chemical synthesis Benzyl Alcohols - chemistry Chemistry Combinatorial Chemistry Techniques Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Magnetic Resonance Spectroscopy Molecular Structure Organic chemistry Preparations and properties Quinones - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	The Diels−Alder reactions of o-quinone methides generated from OBOC-salicylic aldehydes and alcohols are described, allowing for the synthesis of various substituted benzopyrans. The low temperatures employed for this procedure enable high diastereoselectivity in reactions with β-substituted o-quinone methides.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo020224v