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• 58518-86-8 4-nitro-1-phenylbutan-1-one 

Relevant academic research and scientific papers

Microbial biotransformations in water/organic solvent system. Enantioselective reduction of aromatic β- and γ-nitroketones

The production of single enantiomers of γ and β-nitroalcohols by microbial bioreduction has been studied. A restricted screening among 14 yeasts was performed using 1-phenyl-4-nitro-1-butanone 1 as substrate. Pichia minuta (CBS 1708) and Pichia etchellsii

Selectivity of Daucus carota roots and baker's yeast in the enantioselective reduction of γ-nitroketones

The enantioselective reduction of a series of aromatic γ-nitroketones was achieved by using Daucus carota roots in water, which afforded the corresponding (S)-alcohols with ees ranging from 73% to 100%. A comparison of these results with the data obtained by reducing the same substrates with baker's yeast resulted in D. carota always being more enantioselective than baker's yeast, although a lower number of substrates were reduced. The possible influence of the aromatic ring substituents on the reaction outcome is also discussed.

Lyophilised yeasts: Easy-to-handle biocatalysts for stereoselective reduction of ketones

The use of lyophilised yeasts as biocatalysts for the reduction of carbonyl compounds has been studied. First, a comparison of the performances of fresh and lyophilised cells of seven yeasts was performed using ethyl acetoacetate and acetophenone as typical substrates. Lyophilised cells gave from low to high conversions but, with a few exceptions, always good enantioselectivity, and they were then employed for the reduction of structurally different carbonyl compounds. Highly enantioselective reduction of carbonyls was often achieved, even with aromatic ketones. Both enantiomers of the alcohols were, in most cases, obtained with high enantiomeric excess by simply choosing a suitable yeast.

Synthesis of enantiopure 2,7-diaryl-1,6-dioxaspiro[4.4]nonanes via enantioselective reduction of prochiral γ-nitroketones by diisopinocampheylchloroborane (DIP-Cl(TM))

The enantioselective reduction of γ-nitroketones 1-4 and γ-nitrodiketones 5-6 by the chiral reducing agent (+)- or (-)-diisopinocampheylchloroborane (DIP-Cl(TM)) afforded respectively nitroalcohols 7-9 with e.e's ranging from 33 to 86% and nitrodiols 11-12 with complete diastereoselectivity and e.e. > 95%. Nitrodiols (1S,7S)-11 and (1S,7S)-12 were then used as chiral precursors for the synthesis of the enantiopure 2,7-diphenyl- and 2,7-di-(2'-methoxyphenyl)-2,6-dioxaspiro[4.4]nonanes, 21 and 22, as EE/ZZ mixtures.

Baker's yeast reduction of prochiral γ-nitroketones: Enantioselective synthesis of (S)-4-nitroalcohols

The baker's yeast reduction of seven different prochiral nitroketones 1a-g occurred on the re face of the carbonyl group, thus affording the (S)-nitroalcohols 2a-g, with different level of enantioselectivity (e.e. 15-99%). The best results (e.e. = 99%) we