Synthesis of Substituted Acetylenic Epoxides Followed by Indium-Catalyzed Rearrangement to 2,3,5-Trisubstituted Furans

Syntheses of various aromatic and aliphatic 2,3,5-trisubstituted furans from acetylenic epoxides are described. These epoxides are directly prepared by nucleophilic ring closure of propargylic alkoxides generated by lithium acetylide addition to α-haloketones.

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Veröffentlicht in:	Journal of organic chemistry 2011-04, Vol.76 (7), p.2379-2383
Hauptverfasser:	Kang, Jun Yong, Connell, Brian T
Format:	Artikel
Sprache:	eng
Schlagworte:	Aliphatic compounds Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Kinetics and mechanisms Organic chemistry Preparations and properties Reactivity and mechanisms
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Beschreibung
Zusammenfassung:	Syntheses of various aromatic and aliphatic 2,3,5-trisubstituted furans from acetylenic epoxides are described. These epoxides are directly prepared by nucleophilic ring closure of propargylic alkoxides generated by lithium acetylide addition to α-haloketones.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo2001353