三氟甲基化
立体中心
对映选择合成
化学
双功能
试剂
酮
硅烷化
组合化学
串联
有机化学
催化作用
三氟甲基
烷基
材料科学
复合材料
作者
Bo‐Shuai Mu,Yang Gao,Yang Fu-ming,Wen‐Biao Wu,Ying Zhang,Xin Wang,Jin‐Sheng Yu,Jian Zhou
标识
DOI:10.1002/anie.202208861
摘要
We report the development of bifunctional trifluoromethylsilyl reagents for selective trifluoromethylation. The newly developed reagent, Me2 (CH2 Cl)SiCF3 , allows highly enantioselective trifluoromethylations of ketones with broad scope. Notably, by taking advantage of the chloromethyl group, a tandem synthesis of chiral trifluoromethylated oxasilacyclopentanes is developed, paving way to α-CF3 tertiary alcohols with vicinal tertiary or quaternary stereocenters. Theoretical studies revealed the important role of nonclassical C-H⋅⋅⋅F-C interactions in stabilizing the transition state, and that the presence of the chlorine atom enhances such interactions for better enantiofacial control.
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