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

doi:10.1246/cl.1997.797

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	797-798
Number of pages	2
Journal	Chemistry Letters
Issue number	8
DOIs	https://doi.org/10.1246/cl.1997.797
Publication status	Published - 1997 Jan 1

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Chemistry(all)

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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. / Sugai, Takeshi; Yokoyama, Masahiro; Yamazaki, Takahiro; Ohta, Hiromichi.

In: Chemistry Letters, No. 8, 01.01.1997, p. 797-798.

Research output: Contribution to journal › Article › peer-review

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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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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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