Highly enantio- and diastereoselective synthesis of β-methyl-γ- monofluoromethyl-substituted alcohols

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.

Citation
Yang, W., Wei, X., Pan, Y., Lee, R., Zhu, B., Liu, H., … Tan, C.-H. (2011). Highly Enantio- and Diastereoselective Synthesis of β-Methyl-γ-monofluoromethyl-Substituted Alcohols. Chemistry - A European Journal, 17(29), 8066–8070. doi:10.1002/chem.201100929

Acknowledgements
We 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.

Publisher
Wiley

Journal
Chemistry - A European Journal

DOI
10.1002/chem.201100929

PubMed ID
21656593

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