Catalytic Asymmetric Acylation of Racemic Scondary Alcohols with Benzoyl Chloride in the Presence of a Chiral Diamine

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Nonenzymatic kinetic resolution of racemic secondary alcohols is an efficient synthetic method to obtain optically active compounds in organic chemistry. Catalytic asymmetric acylation of racemic secondary alcohols has been successfully performed with achiral benzoyl chloride in the presence of only 0.3 mol% of chiral diamine (<B>3</B>) derived from (<I>S</I>)-proline, combined with 0.5 equivalent of triethylamine. This asymmetric acylation of various racemic cyclic secondary alcohols, 5, 6, or 8 membered cycloalkanols (<B>1a–1c</B>), hydroxyesters (<B>1d</B> and <B>1e</B>), and bromohydrins (<B>1f</B> and <B>1g</B>) gave the corresponding optically active benzoates (84–97% ee) and unreacted alcohols (79–95% ee). Racemic acyclic secondary alcohols (<B>1h–1j</B>) were also acylated in moderate enantioselectivity.

収録刊行物

  • Chemistry letters  

    Chemistry letters 1999(3), 265-266, 1999-03-05 

    公益社団法人 日本化学会

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各種コード

  • NII論文ID(NAID)
    10004340442
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
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