PLE catalysed enantiomeric separation of various (+/-)-6-acetoxy-alpha,beta-unsaturated cyclic ketones

Tanyeli, Cihangir
Dikici, E
Fleischhauer, J
Repges, C
Wang, YK
Gawronski, J
Kacprzak, K
Various (+/-)-6-acetoxy-alpha,beta -unsaturated cyclic ketones were resolved by PLE catalysed hydrolysis to afford enantiomerically enriched 6-hydroxy derivatives with 85-98% e.e. The absolute configuration of 6-hydroxy-alpha,beta -unsaturated cyclic ketones were determined via CD measurements.


PLE catalyzed enantiomeric separation of (+/-)-2-furylcarbinols
Tanyeli, Cihangir; Arkin, Ali Hakan; Akhmedov, Idris Mecidoğlu (1997-01-01)
O-Acetyl derivatives of (+/-)-2-furylcarbinols were resolved by PLE catalyzed hydrolysis to afford optically active 2-furylcarbinols in up to 98% e.e. that are valuable chiral building blocks in the synthesis of various biologically active compounds. Enantiomeric excess values were determined by using H-1-NMR and GC analysis of (S)-O-acetyllactyl ester derivatives of 2-furylcarbinols. They were also correlated with the Literature values.
PLE and HLE catalyzed reverse enantiomeric separation of (±)-methyl-2- methoxy-1-methyl-2,5-cyclohexadiene-1-carboxylate derivatives
Tanyeli, Cihangir; Demir, Ayhan Sıtkı; ALVES, Rosemeire Brondi; ARSENİYADİS, Simeon (1999-03-26)
We describe the diversities of hydrolase-type enzymes PLE and HLE on the hydrolysis of (+/-)-methyl-2-methoxy-1 -methyl-2,5-cyclohexadiene-1-carboxylate and (+/-)-methyl-2-methoxy-1 -methyl-2,5-cyclohexadiene-4-one-1-carboxylate to afford both enantiomers with 92-96% ee.
CCL- and PLE-catalyzed reverse enantiomeric separation of various (+/-)-2-thienylcarbinols
Tanyeli, Cihangir; Ozdemirhan, D (2001-01-01)
(+/-)-2-Thienylcarbinols and their O-acetyl derivatives were resolved in reverse separation by CCL and PLE catalysed hydrolysis to afford optically active 2-thienylcarbinols in 35%-99% e.e. that are valuable chiral building blocks, in particular in the synthesis of pheromones and some alkoloid type natural products. Absolute configurations were determined by the correlation of specific rotation values with the literature and by transforming into the corresponding secondary alcohols via reductive desulfuriza...
Fam-zinc catalyzed asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides and
Koyuncu, Hasan; Doğan, Özdemir; Department of Chemistry (2007)
In the first part of this study, four new chiral ligands (FAM) were synthesized and used in catalytic amounts in asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides. This method leads to the synthesis of chiral pyrrolidines, which are found in the structure of many biologically active natural compounds and drugs. It was found that using 10 mol% of one of these chiral ligands with different dipolarophiles (dimethyl maleate, dimethyl fumarate, methyl acrylate, tert-butyl acrylate, and Nmethylm...
Mn(OAc)3 promoted addition of an active methylene compound to alkenes: mechanistic studies
Ceyhan, Selin; Balcı, Metin; Department of Chemistry (2015)
Radical cyclization of alkenes is one of the most important methods for the synthesis of cyclic compounds. The one electron oxidant Mn(OAc)3 has been used for many years for the oxidative addition of acetic acid to alkenes to give lactones. In this thesis, various alkenes substituted at 1,2-positions by phenyl and thiophene rings were reacted with active methylene compounds in the presence of Mn(OAc)3∙2H2O. The regioselectivity of the addition were searched. The mechanism for the addition was studied in con...
Citation Formats
C. Tanyeli et al., “PLE catalysed enantiomeric separation of various (+/-)-6-acetoxy-alpha,beta-unsaturated cyclic ketones,” ENANTIOMER, pp. 219–227, 2001, Accessed: 00, 2020. [Online]. Available: