Chemoenzymatic synthesis of chiral a-hydroxy heterocyclic ketones

Aybey, Asuman


Chemoenzymatic synthesis of various spiro cyclopentenone-pyran and spiro dihydropyran compounds
Ozdemirhan, Fazilet Devrim; Tanyeli, Cihangir; Guzel, Ayca (2012-08-19)
Chemoenzymatic synthesis of 2-ethyl-5-hydroxy-3- methoxy-cyclopent-2-enone
Dalfidan, Çağla; Demir, Ayhan Sıtkı; Department of Chemistry (2005)
Chiral hydroxylated cyclopentane derivatives are important precursors for biologically active compounds. Synthesis of these types of compounds in optically pure form found increased interest in pharmaceutical chemistry. 2-ethyl-cyclopentane-1.3-dione was acetoxylated using manganese III acetate at preferred positions. Enzyme catalyzed enantioselective hydrolysis or enantioselective acetoxylation of hydrolyzed acetoxy derivatives gives the corresponding hydroxylated diketones in optically pure form.
Chemoenzymatic synthesis of alpha(1)- and alpha-acetoxylated cyclic ketones
Tanyeli, Cihangir; Akhmedov, M (Elsevier BV, 2004-06-07)
alpha,beta-Unsaturated and saturated cyclic ketones were selectively oxidized at the alpha'- and alpha-positions using Mn(OAc)(3) and Pb(OAc)(4), respectively, resulting in high chemical yields. The resultant racemic alpha'- and alpha-acetoxylated substrates were resolved into corresponding enantiomerically enriched alpha'- and alpha-hydroxylated and acetoxylated compounds with 96-98% ee via PLE hydrolysis. The absolute configurations of alpha'-acetoxy-alpha,beta-unsaturated cyclic ketones were determined b...
Syntheses, electrochemical and spectroelectrochemical characterizations of quinoxaline-based conjugated polymers for organic photovoltaics
Yasa, Mustafa; Göker, Seza; Udum, Yasemin Arslan; Günbaş, Emrullah Görkem; Toppare, Levent Kamil (2017-04-02)
Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives
ÖZDEMİRHAN, FAZİLET DEVRİM; ÇELİK, MURAT; ATLI, SELİN; Tanyeli, Cihangir (Elsevier BV, 2006-01-23)
Racemic alpha'-acetoxy alpha,beta-unsaturated cyclopentanone and cyclohexanone have been resolved into the corresponding enantiomerically enriched alpha'-hydroxylated and acetoxylated compounds with 96-97% ee via PLE hydrolysis. Stereoselectivity in the palladium(II)-catalyzed reaction between the enantiomerically enriched alpha'-acetoxylated compounds and diazomethane has been investigated. In the alpha'-acetoxylated cyclopentenone, preferential cyclopropanation occurs in the anti-form, whereas alpha'-acet...
Citation Formats
A. Aybey, “Chemoenzymatic synthesis of chiral a-hydroxy heterocyclic ketones,” M.S. - Master of Science, Middle East Technical University, 2003.