Regioselective Preparation of 2, 4-, 3, 4-, and 2, 3, 4-Substituted Furan Rings. 1.[1, 4] O→ C and [1, 4] C→ O Silyl Migrations of Silyl Ethers and Esters Attached to …

E Bures, PG Spinazzé, G Beese, IR Hunt…

文献索引：Bures, Edward; Spinazze, Patrick G.; Beese, Giovanna; Hunt, Ian R.; Rogers, Christine; Keay, Brian A. Journal of Organic Chemistry, 1997 , vol. 62, # 25 p. 8741 - 8749

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被引用次数: 37

摘要

[1, 4] O→ C and [1, 4] C→ O rearrangements are described for a variety of furans and thiophenes. Treatment of 3-((silyloxy) methyl) furans and-thiophenes with n-BuLi in HMPA provided 2-silylated-3-(hydroxymethyl) furans and-thiophenes in good to excellent yields. The reaction was shown by crossover studies to proceed via an intramolecular [1, 4] O→ C silyl migration. Silyl esters of 3-furoic acids also underwent an intramolecular [1, 4] O→ C ...