Please use this identifier to cite or link to this item: https://doi.org/10.1002/chem.201100929
Title: Highly enantio- and diastereoselective synthesis of β-methyl-γ- monofluoromethyl-substituted alcohols
Authors: Yang, W.
Wei, X.
Pan, Y.
Lee, R.
Zhu, B.
Liu, H.
Yan, L.
Huang, K.-W.
Jiang, Z.
Tan, C.-H. 
Keywords: alcohols
asymmetric catalysis
FBSM
Morita-Baylis-Hillman reactions
organocatalysis
Issue Date: 11-Jul-2011
Source: Yang, W., Wei, X., Pan, Y., Lee, R., Zhu, B., Liu, H., Yan, L., Huang, K.-W., Jiang, Z., Tan, C.-H. (2011-07-11). Highly enantio- and diastereoselective synthesis of β-methyl-γ- monofluoromethyl-substituted alcohols. Chemistry - A European Journal 17 (29) : 8066-8070. ScholarBank@NUS Repository. https://doi.org/10.1002/chem.201100929
Abstract: Enanatiopure 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.
Source Title: Chemistry - A European Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/93942
ISSN: 09476539
DOI: 10.1002/chem.201100929
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