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    Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations

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    Type
    Article
    Authors
    Yang, Limin
    Wang, Fei
    Lee, Richmond
    Lv, Yunbo
    Huang, Kuo-Wei cc
    Zhong, Guofu
    KAUST Department
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2014-07-02
    Online Publication Date
    2014-07-02
    Print Publication Date
    2014-08
    Permanent link to this record
    http://hdl.handle.net/10754/563681
    
    Metadata
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    Abstract
    A facile N-heterocyclic carbene catalytic enantioselective aza-Diels-Alder reaction of oxodiazenes with α-chloroaldehydes as dienophile precursors is reported, with excellent enantioselectivity (ee > 99%) and excellent yield (up to 93%). DFT study showed that cis-TSa, formed from a top face approach of oxodiazene to cis-IIa, is the most favorable transition state and is consistent with the experimental observations. © 2014 American Chemical Society.
    Citation
    Yang, L., Wang, F., Lee, R., Lv, Y., Huang, K.-W., & Zhong, G. (2014). Asymmetric NHC-Catalyzed Aza-Diels–Alder Reactions: Highly Enantioselective Route to α-Amino Acid Derivatives and DFT Calculations. Organic Letters, 16(15), 3872–3875. doi:10.1021/ol501424f
    Sponsors
    We thank the NSFC (21302032 and 21373073) and the PCSIRT (IRT 1231) for financial support. G.Z. appreciates a QjanJiang Scholar from Zhejiang Province in China.
    Publisher
    American Chemical Society (ACS)
    Journal
    Organic Letters
    DOI
    10.1021/ol501424f
    PubMed ID
    24987938
    Relations
    Is Supplemented By:
    • [Dataset]
      Yang, L., Wang, F., Lee, R., Lv, Y., Huang, K.-W., & Zhong, G. (2014). CCDC 881370: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccyl49y. DOI: 10.5517/ccyl49y HANDLE: 10754/624714
    ae974a485f413a2113503eed53cd6c53
    10.1021/ol501424f
    Scopus Count
    Collections
    Articles; Biological and Environmental Sciences and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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