Preparative Biotransformations: Oxidation of Alcohols

Abstract

Winning the primaries: Oxidation of primary and secondary alcohols, to their corresponding aldehydes or carboxylic acids and ketones respectively, are among the most important reactions in organic synthesis. In this Minireview we cover the oxidation of alcohols by biotransformation.

Microbial Engineering for Aldehyde Synthesis

“…In this case, spontaneous decarboxylation of a C n hydroperoxy fatty acid intermediate provides a driving force for aldehyde generation. The dioxygenasecatalyzed reaction is as follows: R-CH 2 -COOHϩO 2 →R-CHOϩCO 2 ϩ H 2 O (4) In addition, aldehydes can be obtained by enzymatic oxidation of primary alcohols (37)(38)(39)(40). From a de novo aldehyde synthesis perspective, these reactions are less relevant given that alcohols are typically produced via aldehyde intermediates.…”

Chemoenzymatic Synthesis in Flow Reactors: A Rapid and Convenient Preparation of Captopril

“…Our flow‐based synthetic route to obtain captopril includes a first biocatalyzed heterogeneous regio‐ and stereoselective oxidation reaction starting from a cheap prochiral diol (2‐methyl‐1,3‐propandiol, 1 ) followed, after isolation of carboxylic acid 2 , by three sequential chemical steps. The biocatalyzed flow oxidation offers an efficient alternative for environmentally benign oxidations in answer to the critical economic and environmental issues that urgently demand greener, more atom‐efficient and scalable oxidation methods . The oxidation was performed using Acetobacter aceti MIM 2000/28; this strain is able to completely convert the substrate into ( R )‐3‐hydroxy‐2‐methylpropanoic acid ( 2 ) with an excellent ee (96–97 %) using a conventional batch‐mode biotransformation.…”

“…The biocatalyzed flow oxidation offers an efficient alternative for environ-mentally benigno xidations in answer to the criticale conomic and environmental issues that urgentlyd emandg reener,m ore atom-efficient and scalableo xidation methods. [8,9] The oxidation wasp erformed using Acetobacter aceti MIM 2000/28; [10][11][12] this strain is ablet oc ompletely convert the substrate into (R)-3-hydroxy-2-methylpropanoic acid (2)w ith an excellent ee (96-97 %) using ac onventionalb atch-mode biotransformation. To exploit all the advantages of performing (bio)catalyzed reactions in flow,i np articulart he high local concentrationo ft he biocatalyst, [13][14][15][16] A. aceti has been immobilized as dried alginate-entrapped cells, that are economical, easyt op repare and can be efficiently used in ap acked bed column.…”

Comparative Catalytic Evaluation of Nano-ZrOx Promoted Manganese Catalysts: Kinetic Study and the Effect of Dopant on the Aerobic Oxidation of Secondary Alcohols

“…The catalytic oxidation of alcohols to carbonyl compounds is one of the most valuable and significant organic transformations in synthetic chemistry from the scientific and manufacturing perspective [1][2][3][4][5]. The oxidation products are significant intermediates in perfumes, confectionary, flameretardants, dyestuffs, cosmetics, agrochemical, and pharmacological industries [6][7][8][9].…”