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Z. Naturforsch. 2013, 68b, 811 – 817
doi:10.5560/ZNB.2013-3051
Diastereoselective 1,3-Dioxolane Formation by Photocatalytic Ring Opening of α-Epoxyketones
Hamid Reza Memarian and Sakineh Zare
Department of Chemistry, University of Isfahan, 81746-73441 Isfahan, Iran
Reprint requests to Prof. Hamid R. Memarian. Fax: +98-311-6689732. E-mail: memarian@sci.ui.ac.ir
Received February 16, 2013 / published online July 19, 2013
Photocatalytic ring opening of α-epoxyketones by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in acetone resulted in the diastereoselective formation of 1,3-dioxolanes through Cα–O bond cleavage. The facility of the ring opening is influenced by the nature and the location of the additional substituent on the α-epoxyketones.
Key words: DDQ, Electron Transfer, α-Epoxyketones, Photocatalyst, Ring Opening
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