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

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.