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Synthesis 1987; 1987(9): 811-814
DOI: 10.1055/s-1987-28081
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A Novel Method for Furan Annelation by the Regioselective Acylation of Allylic Sulfides via α-Silyl Intermediates

Kunio Hiroi* , Hiroyasu Sato
  • *Department of Synthetic Organic Chemistry, Tohoku College of Pharmacy, 4-4-1 Komatsushima, Sendai, Miyagi 983, Japan
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Publikationsdatum:
12. September 2002 (online)

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Aluminum chloride-catalyzed acylations of allylic phenyl sulfides 3 with acid chlorides 5 were carried out via α-silyl intermediates 4 to give γ-acylated vinylic sulfides 6 with complete regioselectivity. Treatment of the γ-acylated compounds with concentrated sulfuric acid in refluxing benzene led to the formation of α-phenylthiofurans 7, which on reductive desulfurization with Raney nickel afforded various furan derivatives 8.