An Efficient Chemoenzymatic Synthesis of S-(-)-Fenpropimirph (CROSBI ID 113900)
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Podaci o odgovornosti
Avdagić, Amir ; Cotarca, L. ; Ružić, K.S. ; Gelo, Mirjana ; Šunjić, Vitomir
engleski
An Efficient Chemoenzymatic Synthesis of S-(-)-Fenpropimirph
First enantioselective synthesis of S-(-)-1-[3-(4-tert-butylphenyl)-2-methyl]propyl-cis-3, 5-dimethylmorpholine (6), biologically active enantiomer of the systematic fungicide fenpropimorph, is reported. It comprises reacting 4-tert-butylbenzylbromide with methyldiethylmalonate, decarbethoxylation of 2 into racemic 3-(4-tert-butylphenyl)-2-methylpropionic acid ethylester (3) in DMSO in the presence of alkali, then Pseudomonas sp. lipase catalyzed kinetic resolution of racemic 3 into S-(+)-acid (4), base-catalyzed racemization and recycling of the R-(-)-ester 3, acylation of cis-3, 5-dimethylmorpholine, and final reduction of the intermediary amide 5 to provide enantiomerically pure S-(-)-6.
Kinetic resolution; 3-(4-terc-butylphenyl)-2-methylpropionic acid ethylester; Pseudomonas sp. lipase
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