Electrophilic fluorination-nucleophilic addition reaction mediated by Selectfluor: Mechanistic studies and new applications

SP Vincent, MD Burkart, CY Tsai, Z Zhang…

文献索引：Vincent, Stephane P.; Burkart, Michael D.; Tsai, Chung-Ying; Zhang, Zhiyuan; Wong, Chi-Huey Journal of Organic Chemistry, 1999 , vol. 64, # 14 p. 5264 - 5279

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被引用次数: 138

摘要

The electrophilic fluorination-nucleophilic addition reaction with Selectfluor-type reagents upon glycals has been studied and optimized. This reaction leads to selective fluorination at the 2-position with concomitant nucleophilic addition to the anomeric center. To understand the stereochemical outcome of this process, a mechanistic study has led to the discovery that, in the fucose series, Selectfluor adds specifically in a syn manner, yielding a 1-[TEDA ...