Add time:07/11/2019         Source:sciencedirect.com

(Z)-3-XCH2-4-(C6H5)-3-buten-2-one enones (X = SCN, N3, SO2Me, OC6H5) were synthesized and submitted to biotransformations using whole Saccharomyces cerevisiae cells. The enone (X = SCN) produced (R)-4-(phenyl)-3-methylbutan-2-one (R)-6 with 93% ee and enones (X = N3, SO2Me, OC6H5) yielded a mixture of (R)-6 and the corresponding CC bond reduction products. Biotransformation with enone (X = N3) mediated by Saccharomyces cerevisiae resulted in two products via two different routes: (i) the ketone (R)-4-azido-3-benzylbutan-2-one in 28% yield and with >99% ee by CC bond reduction; (ii) ketone (R)-6 in 51% yield and with 95% ee via cascade reactions beginning with azido group displacement by the formal hydride from flavin mononucleotide in an SN2′ type reaction followed by reduction of the newly formed CC bond.

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