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

• Takeshi Sugai

  Department of Chemistry, Keio University3-14-1 Hiyoshi, Yokohama

• Masahiro Yokoyama

  Department of Chemistry, Keio University3-14-1 Hiyoshi, Yokohama

• Takahiro Yamazaki

  Department of Chemistry, Keio University3-14-1 Hiyoshi, Yokohama

• Hiromichi Ohta

  Department of Chemistry, Keio University3-14-1 Hiyoshi, Yokohama

抄録

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. (E)-3-Carbamoyl-1-propenylboronic acid was obtained by an incubation of the corresponding nitrile with Rhodococcus rhodochrous IFO 15564. Palladium(0)-catalyzed cross-coupling reaction of the product with (E)- and (Z)-bromoalkenes afforded the (3E,5E)- and (3E,5Z)-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 26 (8), 797-798, 1997-08-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360565169062821376
• NII論文ID: 10002614120
• NII書誌ID: AA00603318
• DOI: 10.1246/cl.1997.797
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/26/8/797/56075400/cl.1997.797.pdf
• データソース種別:
  • Crossref
  • CiNii Articles