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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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. (<I>E</I>)-3-Carbamoyl-1-propenylboronic acid was obtained by an incubation of the corresponding nitrile with <I>Rhodococcus rhodochrous</I> IFO 15564. Palladium(0)-catalyzed cross-coupling reaction of the product with (<I>E</I>)- and (<I>Z</I>)-bromoalkenes afforded the (3<I>E</I>,5<I>E</I>)- and (3<I>E</I>,5<I>Z</I>)-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.
- Chemistry Letters
Chemistry Letters 1997(8), 797-798, 1997-08
The Chemical Society of Japan