Highly enantio- and diastereoselective synthesis of β-methyl-γ- monofluoromethyl-substituted alcohols
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2011-06-07
Print Publication Date2011-07-11
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
RelationsIs Supplemented By:
Yang, 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. DOI: 10.5517/ccw1z62 HANDLE: 10754/624625
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. DOI: 10.5517/ccw1z73 HANDLE: 10754/624626
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