Preparation of optically active secondary alcohols by combination of enzymatic hydrolysis and chemical transformation

Fungal mediated kinetic resolution of racemic acetates to ( R )-alcohols using Fusarium proliferatum

“…Enzyme mediated kinetic resolution of such alcohols using lipases, esterases, and alcohol dehydrogenases have been reported in the literature. [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] For example, resolution of (±)-lavandulol has been achieved previously with various lipases such as Candida antarctica lipase B (CAL B), 9 Hog pancreas lipase, 29 Porcine pancreas lipase, 26 and Yarrowia lipolytica lipases. 30 However, enzyme catalyzed resolution process is associated with several disadvantages such as higher cost, low substrate concentration, instability and cofactor dependency of the enzymes in several occasions.…”

Biotransformation-mediated synthesis of (1S)-1-(2,6-dichloro-3-fluorophenyl)ethanol in enantiomerically pure form

“…10 Thus, the mixture of (R)-2 and (S)-5 initially generated by PLE hydrolysis of 5 was treated with methanesulfonyl chloride (0.5 equiv based on the amount of acetate 5 employed) and the resulting mixture of methanesulfonate (R)-6 and acetate (S)-5 was exposed to potassium acetate at elevated temperature. This two-step process afforded acetate (S)-5 in an acceptable yield (61% for both steps, procedure not optimised) and 97% ee.…”

Biocatalysis Applied to the Synthesis of Agrochemicals

“…WS that catalyzes the asymmetric reduction of 2-chloroacrylic acid to yield (S)-2-chloropropionic acid, with NADPH being a required co-substrate for the reaction. Aryloxypropionic esters and derivatives have also been prepared with esterases [8,9,10,11].…”

“…In addition, Takahashi et al [48,49] also reported an enzymatic process for producing optically active cis-type 1,2-diol derivatives (11), by means of lipase-catalyzed resolution. Derivatives (11) are used as intermediates for producing optically active cis-type azole derivatives (12), which can be used as a fungicide.…”