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

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7 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)797-798
Number of pages2
JournalChemistry Letters
Issue number8
Publication statusPublished - 1997

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Sorbic Acid
Nitriles
Amides
Acids
Bearings (structural)
Enzymes
Palladium
Carboxylic Acids
Microorganisms
Hydrolysis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "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.",
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T1 - Pivotal role of (E)-3-carbamoyl-1-propenylboronic acid in the combination of Suzuki-Miyaura coupling and enzyme reactions

T2 - Synthesis of (3E,5E)-and (3E,5Z)-6-phenyl-3,5-hexadienoic acid

AU - Sugai, Takeshi

AU - Yokoyama, Masahiro

AU - Yamazaki, Takahiro

AU - Ohta, Hiromichi

PY - 1997

Y1 - 1997

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AB - 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.

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