Stereoselective nucleophilic monofluoromethylation of tert-butanesulfinimines: Dynamic thermodynamic Resolution of racemic alpha-fluoro carbanions
Stereoselective nucleophilic monofluoromethylation of tert-butanesulfinimines: Dynamic thermodynamic Resolution of racemic alpha-fluoro carbanions
复制标题
叔丁烷亚亚胺的立体选择性亲核单氟甲基化：外消旋α-氟碳负离子的动态热力学拆分
DOI：
10.1016/j.jfluchem.2020.109451
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发表时间：
2020
影响因子：
1.9
通讯作者：
Hu Jinbo
中科院分区：
文献类型：
--
作者：
Ye Wencho;Ni Chuanfa;Hu Jinbo
以α-氟-α-苯硫基-α-苯磺酰基甲烷（FTSM）为试剂，叔丁基亚磺酰基醛亚胺的非对映选择性亲核单氟甲基化反应得到了α-单氟甲基胺，该反应产率高，对单氟甲基化碳和相邻的含磺酰基的氟代碳均具有良好的立体控制性.在优化的条件下，外消旋α-氟-α-苯硫基-α-苯磺酰甲基阴离子与光学纯的叔丁烷亚磺酰基醛亚胺的加成反应具有可逆性，因而可进行动态热力学拆分.
A diastereoselective nucleophilic monofluoromethylation oftert-butanesulfinyl aldimines with α-fluoro-α-phenylthio-α-phenylsulfonylmethane (FTSM) as the reagent has been developed, which affords α-monofluoromethyl amines in good to excellent yields with excellent stereocontrol on both the monofluoromethylated carbon and the neighboring sulfonyl-bearing fluorinated carbon. The racemic α-fluoro-α-phenylthio-α-phenylsulfonylmethide anions undergo a dynamic thermodynamic resolution due to the reversibility of their addition to the optically puretert-butanesulfinyl aldimines under the optimized conditions.