2,4-Dioxoalkanoates, e.g., AcCH2COCO2Me, and the parent γ-keto-α-enamino esters, e.g., AcCH:C(NH2)CO2Me, are regioselectively reduced by bakers' yeast to (R)-α-hydroxy-γ-ketoesters (R)-RCOCH2CH(OH)CO2R1 (R-I; R, R1 = Me, Et, R = R1 = Me, Et), in moderate to good chem. yield and appreciable enantioselectivity. Enantioselective hydrolysis by pig liver esterase of the acetyl derivs., e.g., AcCH2CH(OAc)CO2Me, easily obtained by acetylation of racemic α-hydroxy-γ-keto esters I, produced the optically active (S)-I in good chem. (60-92%) and optical (53-92%) yield.
Regio - and enantioselective bioreduction of ethyl 2,4-dioxoalkanoates and γ-Keto-α-enamino esters with fermenting baker's yeast
BARALDI, Pier Giovanni;MANFREDINI, Stefano;ROMAGNOLI, Romeo;SIMONI, Daniele;ZANIRATO, Vinicio
1992
Abstract
2,4-Dioxoalkanoates, e.g., AcCH2COCO2Me, and the parent γ-keto-α-enamino esters, e.g., AcCH:C(NH2)CO2Me, are regioselectively reduced by bakers' yeast to (R)-α-hydroxy-γ-ketoesters (R)-RCOCH2CH(OH)CO2R1 (R-I; R, R1 = Me, Et, R = R1 = Me, Et), in moderate to good chem. yield and appreciable enantioselectivity. Enantioselective hydrolysis by pig liver esterase of the acetyl derivs., e.g., AcCH2CH(OAc)CO2Me, easily obtained by acetylation of racemic α-hydroxy-γ-keto esters I, produced the optically active (S)-I in good chem. (60-92%) and optical (53-92%) yield.File in questo prodotto:
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