Palladium–(S,pR)-FerroNPS-Catalyzed Asymmetric Allylic Etherification: Electronic Effect of Nonconjugated Substituents on Benzylic Alcohols on Enantioselectivity

Authors

  • Fuk Loi Lam,

    1. Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis
    2. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong SAR, China, Fax: (+852) 2364-9932
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  • Terry Tin-Lok Au-Yeung Dr.,

    1. Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis
    2. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong SAR, China, Fax: (+852) 2364-9932
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  • Fuk Yee Kwong Dr.,

    1. Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis
    2. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong SAR, China, Fax: (+852) 2364-9932
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  • Zhongyuan Zhou Prof. Dr.,

    1. Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis
    2. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong SAR, China, Fax: (+852) 2364-9932
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  • Kwok Yin Wong Prof. Dr.,

    1. Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis
    2. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong SAR, China, Fax: (+852) 2364-9932
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  • Albert S. C. Chan Prof. Dr.

    1. Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis
    2. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong SAR, China, Fax: (+852) 2364-9932
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  • We thank the University Grants Committee Area of Excellence Scheme (AoE/P-10/01) and The Hong Kong Polytechnic University (Area of Strategic Development) for financial support of this study. FerroNPS refers to a series of P,S ligands with a ferrocenyl motif and an amine linkage.

Abstract

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An enantioselective C[BOND]O bond-forming reaction proceeds well under palladium catalysis with newly developed N–P,S ligands with a ferrocene motif (see scheme). Nonconjugated substituents on the benzylic alcohol substrate lead to an increase in enantioselectivity with increasing electron-donating ability in the title reaction with racemic 1,3-diphenyl-2-propenyl acetate. Cy = cyclohexyl.

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