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
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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
Is Supplemented ByYang, W., Wei, X., Pan, Y., Lee, R., Zhu, B., Liu, H., … Tan, C.-H. (2011). CCDC 806254: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccw1z62
Yang, W., Wei, X., Pan, Y., Lee, R., Zhu, B., Liu, H., … Tan, C.-H. (2011). CCDC 806255: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccw1z73
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