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

Wenguo Yang, Xinle Wei, Yuanhang Pan, Richmond Lee, Bo Zhu, Hongjun Liu, Lin Yan, Kuo-Wei Huang, Zhiyong Jiang, Choonhong Tan

Research output: Contribution to journalArticlepeer-review

61 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)8066-8070
Number of pages5
JournalChemistry - A European Journal
Volume17
Issue number29
DOIs
StatePublished - Jun 7 2011

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
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.

ASJC Scopus subject areas

  • General Chemistry

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