α-fluorination of ketones by xenon and iodobenzene difluorides: A stereochemical evidence demonstrating their mechanistic differences

T Tsushima, K Kawada, T Tsuji

文献索引：Tsushima, Tadahiko; Kawada, Kenji; Tsuji, Teruji Tetrahedron Letters, 1982 , vol. 23, # 11 p. 1165 - 1168

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被引用次数: 44

摘要

Abstract Xenon difluoride reacts smootlhy with various steroid silyl enol ethers in the absence of any acid catalyst to afford stereoselectively α-oriented α-fluoroketones in good yields while iodotoluene difluoride reacts rather sluggishly with these silyl enol ethers to competitively produce β-oriented α-fluoro ketones, elimination and other nucleophilic substitution products. The observed stereochemical contrast clearly suggests an ...