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

Handle URI:
http://hdl.handle.net/10754/561799
Title:
Highly enantio- and diastereoselective synthesis of β-methyl-γ- monofluoromethyl-substituted alcohols
Authors:
Yang, Wenguo; Wei, Xinle; Pan, Yuanhang; Lee, Richmond; Zhu, Bo; Liu, Hongjun; Yan, Lin; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Jiang, Zhiyong; Tan, Choonhong
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.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; KAUST Catalysis Center (KCC); Chemical Science Program; Physical Sciences and Engineering (PSE) Division; HCL
Publisher:
Wiley-Blackwell
Journal:
Chemistry - A European Journal
Issue Date:
7-Jun-2011
DOI:
10.1002/chem.201100929
PubMed ID:
21656593
Type:
Article
ISSN:
09476539
Sponsors:
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.
Is 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:http://hdl.handle.net/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:http://hdl.handle.net/10754/624626
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorYang, Wenguoen
dc.contributor.authorWei, Xinleen
dc.contributor.authorPan, Yuanhangen
dc.contributor.authorLee, Richmonden
dc.contributor.authorZhu, Boen
dc.contributor.authorLiu, Hongjunen
dc.contributor.authorYan, Linen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorJiang, Zhiyongen
dc.contributor.authorTan, Choonhongen
dc.date.accessioned2015-08-03T09:04:52Zen
dc.date.available2015-08-03T09:04:52Zen
dc.date.issued2011-06-07en
dc.identifier.issn09476539en
dc.identifier.pmid21656593en
dc.identifier.doi10.1002/chem.201100929en
dc.identifier.urihttp://hdl.handle.net/10754/561799en
dc.description.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.en
dc.description.sponsorshipWe 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.en
dc.publisherWiley-Blackwellen
dc.subjectalcoholsen
dc.subjectasymmetric catalysisen
dc.subjectFBSMen
dc.subjectMorita-Baylis-Hillman reactionsen
dc.subjectorganocatalysisen
dc.titleHighly enantio- and diastereoselective synthesis of β-methyl-γ- monofluoromethyl-substituted alcoholsen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentHCLen
dc.identifier.journalChemistry - A European Journalen
dc.contributor.institutionKey Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004, Chinaen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore (NUS), 3 Science Drive 3, Singapore 117543, Singaporeen
kaust.authorLee, Richmonden
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByYang, 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/ccw1z62en
dc.relation.isSupplementedByDOI:10.5517/ccw1z62en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624625en
dc.relation.isSupplementedByYang, 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/ccw1z73en
dc.relation.isSupplementedByDOI:10.5517/ccw1z73en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624626en

Related articles on PubMed

All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.