Pivotal Role of (E)-3-Carbamoyl-1-propenylboronic Acid in the Combination of Suzuki-Miyaura Coupling and Enzyme Reactions : Synthesis of (3E, 5E)- and (3E, 5Z)-6-Phenyl-3, 5-hexadienoic Acid

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The first example of the enzyme-catalyzed hydrolysis of a nitrile bearing alkenylboronic acid functionality and its application to the synthesis of dienecarboxylic acids are described. (<I>E</I>)-3-Carbamoyl-1-propenylboronic acid was obtained by an incubation of the corresponding nitrile with <I>Rhodococcus rhodochrous</I> IFO 15564. Palladium(0)-catalyzed cross-coupling reaction of the product with (<I>E</I>)- and (<I>Z</I>)-bromoalkenes afforded the (3<I>E</I>,5<I>E</I>)- and (3<I>E</I>,5<I>Z</I>)-unsaturated amides, respectively. The second incubation of the above amides with the same microorganism provided the carboxylic acids with the defined configuration of conjugated double bonds.

収録刊行物

  • Chemistry letters  

    Chemistry letters 1997(8), 797-798, 1997-08 

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10002614120
  • 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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