Corrigendum to “Resolution of (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (−)- and (+)-proto-quercitol” [Tetrahedron: Asymmetry 15 (2004) 453]

Date

2004-6

Author

Gültekin, M.Serdar
Çelik, Murat
Turkut, Engin
Tanyeli, Cihangir
Balci, Metin

Metadata

Show full item record

Item Usage Stats

207
views

0
downloads

Photooxygenation of cyclohexa-1,4-diene affordedanti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide. The hydro-peroxy endoperoxide was reduced with dimethylsulfide–titanium tetraisopropoxide to produce (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplishedwithCandida cylindracealipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: Thecleavage of the peroxide linkage by thiourea followed by the oxidation of the double bond with OsO4resulted in the formation of())-proto-quercitol and (+)-proto-quercitol, respectively.

URI

https://hdl.handle.net/11511/28176

Journal

Tetrahedron: Asymmetry

DOI

https://doi.org/10.1016/j.tetasy.2004.05.017

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Resolution of (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (-)- and (+)-proto-quercitol GÜLTEKİN, M SERDAR; Celik, M; TURKUT, ENGİN; Tanyeli, Cihangir; BALCİ, METİN (Elsevier BV, 2004-02-09) Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide. The hydroperoxy endoperoxide was reduced with dimethylsulfide-titanium tetraisopropoxide to produce ()-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplished with Candida cylindracea lipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: The cleavage ...
A stable carbonyl-pyrazine-metal(0) complex: Synthesis and characterization of cis-tetracarbonylpyrazinetrimethylphosphitetungsten(0) Alper, Fatma; Kayran, Ceyhan; Özkar, Saim (2006-06-01) Pentacarbonylpyrazinetungsten(0), (CO)(5)W(pyz), is not stable in solution in polar solvents such as acetone or dichloromethane and undergoes conversion to a bimetallic complex, (CO)(5)W(pyz)W(CO)(5) plus free pyrazine. These three species exist at equilibrium. Using the quantitative H-1 NMR spectroscopy, the equilibrium constant could be determined to be K-eq = (5.9 +/- 0.8) x 10(-2) at 25 degrees C. Introducing a second pyrazine ligand into the molecule does not stabilize the complex, as CiS-W(CO)(4)(pyz)...
Effects of High Hydrostatic Pressure Treatment on Water Absorption Properties of Bovine and Fish Gelatin Gültekin, Necmiye Büşra; Alpas, Hami; Öztop, Halil Mecit (null; 2017-06-28) The objective of this study was to investigate the effect of High Hydrostatic Pressure (HHP) treatment on physical properties of bovine (220, 240 and 250 bloom) and fish (240 bloom) gelatins. HHP treatment parameters were chosen as 1,000; 3,000; 5,000 bar at 40°C for 5 min. To obtain information about water absorption and gelation behavior of the treated gelatins, Nuclear Magnetic Resonance (NMR) relaxometry experiments through transverse relaxation time (T2) measurements were conducted. The change...
Synthesis and characterization of fluorine-substituted polyanilines Cihaner, A; Önal, Ahmet Muhtar (Elsevier BV, 2001-09-01) Poly(2-fluoroaniline), P2FAN, poly(3-fluoroaniline). P3FAN. and poly(4-fluoroaniline), P4FAN, have been synthesized from fluorine substituted aniline monomers in aqueous acidic medium using potassium dichromate as oxidizing agent. Characterization of polymer products has been carried out using FTIR, and NMR spectroscopic techniques. Thermal analysis of polyfluoroaniline powders was also investigated using differential scanning calorimetry and thermogravimetric analysis. To compare the structural properties ...
Synthesis of new ferrocenyl substituted quinoxaline derivative monomers, their polymerization and electrochemical behaviors Özdemir, Şerife; Doğan, Özdemir; Toppare, Levent Kamil; Department of Chemistry (2010) 5,8-Bis(2,3-dihydrothieno[3,4b][1,4]dioxin-5-yl)-2-(naphthalen-2-yl)-3-ferrocenyl-4a,8a-dihydroquinoxaline (DEFNQ), 5,8-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2-(phenyl)-3 ferrocenylquinoxaline (DEFPQ) and 5,8-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2,3-di(naphthalen-2-yl)quinoxaline (DEDNQ) were synthesized, electrochemically polymerized and electrochromic properties of resultant polymers were investigated. For the characterization of the monomers Nuclear Magnetic Resonance (1H-NMR, 13C-NMR) w...

Citation Formats

M. S. Gültekin, M. Çelik, E. Turkut, C. Tanyeli, and M. Balci, “Corrigendum to “Resolution of (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (−)- and (+)-proto-quercitol” [Tetrahedron: Asymmetry 15 (2004) 453],” Tetrahedron: Asymmetry, pp. 1959–1960, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/28176.