[2, 3]-Sigmatropic rearrangement of an in situ prepared ylide and a thio ether to thio ester conversion as key steps in short syntheses of sarkomycin and its phenyl thio …

T Cohen, Z Kosarych, K Suzuki…

文献索引：Cohen, Theodore; Kosarych, Zenyk; Suzuki, Kunio; Yu, Lin-Chen Journal of Organic Chemistry, 1985 , vol. 50, # 16 p. 2965 - 2968

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被引用次数: 33

摘要

2-[(Phenylthio) methyl] cyclopent-2-en-l-one (Z), which is readily available by the reaction of 2-cyclopentenone with thiophenol, formaldehyde, and triethylamine, is transformed, in high yield and moderate conversion by treatment with (trimethylsily1) methyl triflate, cesium fluoride, and benzaldehyde, to 2-methylene-3-[(phenylthio) methyl] cyclopentanone (3), which, by the use of trichloroisocyanuric acid (Chloreal), can be quantitatively ...