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

Takeshi Sugai, Masahiro Yokoyama, Takahiro Yamazaki, Hiromichi Ohta

研究成果: Article査読

7 被引用数 (Scopus)

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.

本文言語English
ページ(範囲)797-798
ページ数2
ジャーナルChemistry Letters
8
DOI
出版ステータスPublished - 1997 1 1

ASJC Scopus subject areas

  • 化学 (全般)

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「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」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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