Oxidative rearrangement of 2-furylcarbamates with dimethyldioxirane: a high-yielding preparation of 5-hydroxypyrrol-2(5H)-ones

A mild, general and efficient method for the oxidative rearrangement of 2-furylcarbamates to N-Boc-5-hydroxypyrrol-2(5H)-ones is reported. The feasibility of removing the Boc group from the products was demonstrated by the synthesis of two hitherto unknown 5-aryl-5-hydroxypyrrol-2(5H)-ones.

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Bibliographische Detailangaben
Veröffentlicht in:	Tetrahedron letters 2011-09, Vol.52 (39), p.5047-5050
Hauptverfasser:	Boukouvalas, John, Loach, Richard P., Ouellet, Etienne
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Curtius rearrangement Exact sciences and technology Feasibility Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic compounds with only one n hetero atom and condensed derivatives Lactam Magnesium perchlorate Organic chemistry Oxidation Preparations and properties Shioiri–Yamada reagent Synthesis (chemistry) Tetrahedrons
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Beschreibung
Zusammenfassung:	A mild, general and efficient method for the oxidative rearrangement of 2-furylcarbamates to N-Boc-5-hydroxypyrrol-2(5H)-ones is reported. The feasibility of removing the Boc group from the products was demonstrated by the synthesis of two hitherto unknown 5-aryl-5-hydroxypyrrol-2(5H)-ones.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2011.07.084