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    The origin of enantioselectivity in the l-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: Effects of the intramolecular hydrogen bonding

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    Type
    Article
    Authors
    Lee, Richmond
    Zhong, Fangrui
    Zheng, Bin cc
    Meng, Yuezhong
    Lu, Yixin
    Huang, Kuo-Wei cc
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2013
    Permanent link to this record
    http://hdl.handle.net/10754/562513
    
    Metadata
    Show full item record
    Abstract
    l-Threonine-derived phosphine-sulfonamide 4 was identified as the most efficient catalyst to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions, affording the desired aza-MBH adducts with excellent enantioselectivities. Density functional theory (DFT) studies were carried out to elucidate the origin of the observed enantioselectivity. The importance of the intramolecular N-H⋯O hydrogen-bonding interaction between the sulfonamide and enolate groups was identified to be crucial in inducing a high degree of stereochemical control in both the enolate addition to imine and the subsequent proton transfer step, affording aza-MBH reactions with excellent enantioselectivity. © 2013 The Royal Society of Chemistry.
    Citation
    Lee, R., Zhong, F., Zheng, B., Meng, Y., Lu, Y., & Huang, K.-W. (2013). The origin of enantioselectivity in the l-threonine-derived phosphine–sulfonamide catalyzed aza-Morita–Baylis–Hillman reaction: effects of the intramolecular hydrogen bonding. Organic & Biomolecular Chemistry, 11(29), 4818. doi:10.1039/c3ob40144h
    Sponsors
    We are grateful for the generous financial support from King Abdullah University of Science and Technology to K.-W.H. and from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-494-112) to Y. L.
    Publisher
    Royal Society of Chemistry (RSC)
    Journal
    Organic & Biomolecular Chemistry
    DOI
    10.1039/c3ob40144h
    PubMed ID
    23774825
    ae974a485f413a2113503eed53cd6c53
    10.1039/c3ob40144h
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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