Highly enantio- and diastereoselective synthesis of β-methyl-γ- monofluoromethyl-substituted alcohols
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
KAUST Catalysis Center (KCC)
Chemical Science Program
Physical Sciences and Engineering (PSE) Division
Permanent link to this recordhttp://hdl.handle.net/10754/561799
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AbstractEnanatiopure β-methyl-γ-monofluoromethyl alcohols were prepared from the allylic alkylation between fluorobis(phenylsulfonyl)methane with Morita-Baylis-Hillman carbonates. The reaction was catalyzed by using the Cinchona alkaloid derivative, (DHQD)2AQN. The origin of the stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed stereoselectivity. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
SponsorsWe are grateful for the financial support from NSFC (21072044) to Z.J., Henan Province International Cooperation Foundation (104300510062) to Z.J. and C.-H.T., and KAUST (4000000076) to K.-W.H.
JournalChemistry - A European Journal
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