Microbial Synthesis of Optically Pure α-Methoxy-α-trifluoromethyl-α-phenylacetic Acid

Abstract

Preparatin of optically pure α-methoxy-α-trifluoromethyl-α-phenylacetic acid via microbial asymmetric hydrolysis of cyanohydrin acetate as the key step is described.

Enantioselective hydrolyses with Yarrowia lipolytica: a versatile strain for esters, enol esters, epoxides, and lactones

“…2 Whole microbial cells have also been used to catalyse some esterolytic reactions: interesting examples can be found for both bacteria and fungi, i.e. Bacillus subtilis, 3 Brevibacterium ammoniagenes, 4 Bacillus coagulans, 5 Pichia miso, 6 Rhizopus nigricans, 7 and Rhizopus oryzae. 8 On the other hand, the examples of microbial hydrolysis of epoxides [9][10][11][12] and nitriles [13][14][15] are not so common, while only a few papers describe the hydrolytic conversions by baker's yeast, [16][17][18] although the use of this microorganism is very simple and obviates the need for sterile fermentation equipment.…”

Enantioselective Zirconium-Catalyzed Friedel−Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones

“…The absolute stereochemistry of compound 3a was determined by chemical transformation into the literature-known compound 6 . This was accomplished by an oxidation procedure in analogy to the oxidative cleavage of furans. , Thus pyrrole 3a was oxidized to the Mosher acid amide 6 upon treatment with NaIO 4 in the presence of RuCl 3 (Scheme ).…”