synthesis of pyrazine via chemoselective reduction of b-keto-a-oximino ester using baker's yeast
- synthesis of pyrazine via chemoselective reduction of b-keto-a-oximino ester using baker's yeast
- 모길웅; 박진형; 강순방; 김유승; Youseung Kim; 이재욱; 금교창
- baker's yeast; redcution; chemoselectivity; pyrazine; b-keto-a-oximino ester
- Issue Date
- Journal of molecular catalysis. B, Enzymatic
- VOL 123, 29-34
- The synthesis of pyrazines by the baker’s yeast-mediated reaction of β-keto-α-oximino esters and amides is described. Baker’s yeast reduced oximes selectively over ketones of β-keto-α-oximino esters to give the corresponding β-keto-α-amino ester intermediates, which underwent spontaneous dimerization followed by air-induced aromatization to yield pyrazines. The chemoselective reduction of β-keto-α-oximino amides using baker’s yeast also afforded the corresponding pyrazines. Interestingly, both hydroximes and alkoximes gave the pyrazines by the baker’s yeast-mediated reduction via the corresponding amino ketones, the known precursors of pyrazines. The reaction was strongly dependent upon pH of reaction medium, and gave optimum yields at pH 5. These results demonstrate that pyrazines were synthesized efficiently and eco-friendly using a whole-cell biocatalytic system as an alternative to chemical reduction.
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