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

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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

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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 ...
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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.