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 |
| Publication status | Published - 1997 |
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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, 1997, p. 797-798.Research output: Contribution to journal › Article
}
TY - JOUR
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
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=0031490830&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0031490830&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0031490830
SP - 797
EP - 798
JO - Chemistry Letters
JF - Chemistry Letters
SN - 0366-7022
IS - 8
ER -