Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 37, Pages 11443-11454Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000893
Keywords
amines; difluoromethylation; fluorine; ketimines; nucleophilic addition
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Funding
- NSF of China [20825209, 20772144, 20832008]
- Chinese Academy of Sciences
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The first highly efficient and stereoselective difluoromethylation of structurally diverse N-tert-butylsulfinyl ketimines has been achieved with an in situ generated PhSO2CF2- anion, which provides a powerful synthetic method for the preparation of a variety of structurally diverse homochiral alpha-difluoromethyl tertiary carbinamines, including alpha-difluoromethyl allylic amines and alpha-difluoromethyl propargylamines. The stereocontrol mode of the present diastereoselective difluoromethylation of ketimines was found to be different from that of other known fluoroalkylations of N-tert-butylsulfinyl aldimines, which suggests that a cyclic six-membered transition state may be involved in the reaction.
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