4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 7, Pages 2379-2383

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo2001353

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Funding

  1. Robert A. Welch Foundation [A-1623]

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

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