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

doi:10.1002/chem.201100929

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 journal › Article › peer-review

63 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 language	English (US)
Pages (from-to)	8066-8070
Number of pages	5
Journal	Chemistry - A European Journal
Volume	17
Issue number	29
DOIs	https://doi.org/10.1002/chem.201100929
State	Published - Jun 7 2011

ASJC Scopus subject areas

General Chemistry

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10.1002/chem.201100929

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@article{b44fc6c435914fffb77defc471cb523b,

title = "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. {\textcopyright} 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

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

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.",

year = "2011",

month = jun,

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doi = "10.1002/chem.201100929",

language = "English (US)",

volume = "17",

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journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

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T1 - Highly enantio- and diastereoselective synthesis of β-methyl-γ- monofluoromethyl-substituted alcohols

AU - Yang, Wenguo

AU - Wei, Xinle

AU - Pan, Yuanhang

AU - Lee, Richmond

AU - Zhu, Bo

AU - Liu, Hongjun

AU - Yan, Lin

AU - Huang, Kuo-Wei

AU - Jiang, Zhiyong

AU - Tan, Choonhong

N1 - 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.

PY - 2011/6/7

Y1 - 2011/6/7

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/561799

UR - http://doi.wiley.com/10.1002/chem.201100929

UR - http://www.scopus.com/inward/record.url?scp=84961978585&partnerID=8YFLogxK

U2 - 10.1002/chem.201100929

DO - 10.1002/chem.201100929

M3 - Article

C2 - 21656593

SN - 0947-6539

VL - 17

SP - 8066

EP - 8070

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 29

ER -

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

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CCDC 806255: Experimental Crystal Structure Determination : Methyl 4-fluoro-2-methyl-3-phenyl-4,4-bis(phenylsulfonyl)butanoate

CCDC 806254: Experimental Crystal Structure Determination : Methyl 3-(4-isopropylphenyl)-2-methylene-4,4-bis(phenylsulfonyl)butanoate

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

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 806255: Experimental Crystal Structure Determination : Methyl 4-fluoro-2-methyl-3-phenyl-4,4-bis(phenylsulfonyl)butanoate

CCDC 806254: Experimental Crystal Structure Determination : Methyl 3-(4-isopropylphenyl)-2-methylene-4,4-bis(phenylsulfonyl)butanoate

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