Journal
NATURE COMMUNICATIONS
Volume 8, Issue -, Pages -Publisher
NATURE RESEARCH
DOI: 10.1038/ncomms14841
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Funding
- National Natural Science Foundation of China [21572096, 21602098, 21302088]
- Shenzhen overseas high level talents innovation plan of technical innovation [KQCX20150331101823702]
- Shenzhen special funds [JCYJ20150430160022517]
- National Key Basic Research Program of China (973 Program) [2013CB834802]
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Although great success has been achieved in asymmetric fluoroalkylation reactions via nucleophilic or electrophilic processes, the development of asymmetric radical versions of this type of reactions remains a formidable challenge because of the involvement of highly reactive radical species. Here we report a catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes with commercially available fluoroalkylsulfonyl chlorides as the radical sources, providing a versatile platform to access four types of enantioenriched alpha-tertiary pyrrolidines bearing beta-perfluorobutanyl, trifluoromethyl, difluoroacetyl and even difluoromethyl groups in excellent yields and with excellent enantioselectivity. The key to success is not only the introduction of the CuBr/chiral phosphoric acid dual-catalytic system but also the use of silver carbonate to suppress strong background and side hydroamination reactions caused by a stoichiometric amount of the in situ generated HCl. Broad substrate scope, excellent functional group tolerance and versatile functionalization of the products make this approach very practical and attractive.
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