Enzymatic production of saturated ketones from allylic alcohols

Abstract

Sunzmary Allylic alcohols (e.g., oct-l-en-3-01) are con-contains a tertiary allylic alcohol substituent, is nonverted, in preparative yields, into saturated ketones by reactive. We note that under the reaction conditions Pseudomonas oleovorans and this process is shown to used, ketonization of saturated alcohols, potential interinvolve independent alcohol dehydrogenase and olefin mediates in the reaction pathway from all ylic alcohols, reductase enzymes. occurs readily, with octan-2-01 being the most reactive alcohol tested. I t is apparent from the Table that reduc-

Oxidation ofsec-Alcohols to the Corresponding Ketones byCorynebacterium equi

“…This observation strongly supports path A. Similar reactions of l-octen-3-01 and otherallylic alcohols with the aid of Pseudomonas oleovorans have been reported by May et al 10 ) CIOH21-n-CH=CH2 o 2 Y: 42% thermophilic ethanologenic bacteria 8 ) have been found to have broad substrate specificities including primary and secondary alcohols. Butanol was .the best substrate among secondary alcohols so far tested.…”

Photoinduced isomerization of allyl alcohols to carbonyl compounds using dendrimer disulfide as catalyst

“…Isomerization of allyl alcohols forms an elegant shortcut to carbonyl compounds in a completely atom-economical process that offers several useful applications in natural-product syntheses and in bulk chemical processes [14]. Although many reports described isomerization of allyl alcohols using metal catalysts [15][16][17][18] such as Ru complexes [16,17] and Fe-carbonyl complexes [15,18], isomerization without metal catalyst was quite rare [19]. In this paper, we describe photoinduced isomerization of allyl alcohols to carbonyl compounds using diphenyl disulfide.…”