ol802226k_si_001.pdf (1003.47 kB)

Stereoselective Monofluoromethylation of N-tert-Butylsulfinyl Ketimines Using Pregenerated Fluoro(phenylsulfonyl)methyl Anion

Download (1003.47 kB)
journal contribution
posted on 04.12.2008, 00:00 by Jun Liu, Laijun Zhang, Jinbo Hu
Pregeneration of fluoro(phenylsulfonyl)methyl anion (PhSO2CHF) 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.