Stereoselective monofluoromethylation of N-tert-butylsulfinyl ketimines using pregenerated fluoro(phenylsulfonyl)methyl anion.
Pregeneration of fluoro(phenylsulfonyl)methyl anion (PhSO(2)CHF(-)) paves the way for the efficient and highly stereoselective monofluoromethylation of (R)-N-tert-butylsulfinyl ketimines. The stereocontrol mode of the present diastereoselective monofluoromethylation of ketimines is different from the previously known nucleophilic fluoroalkylation of (R)-N-tert-butylsulfinyl aldimines, which suggests that a cyclic six-membered transition state (rather than a nonchelation controlled one) is involved in the current ketimine reaction.
Liu
Jun
J
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Zhang
Laijun
L
Hu
Jinbo
J
D007097:Imines / Q000737:chemistry*; D008745:Methylation; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013451:Sulfonic Acids / Q000737:chemistry*
D007097:Imines; D009570:Nitriles; D013451:Sulfonic Acids; C542835:ketimine