Journal
ORGANIC LETTERS
Volume 10, Issue 23, Pages 5377-5380Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802226k
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Funding
- National Natural Science Foundation of China [20502029, 20772444, 20825209]
- Chinese Academy of Sciences
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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.
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