Enantioselective copper-catalyzed allylic acetoxylation of cyclohexene |
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| Institution: | 1. Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia;2. Department of Organic Chemistry, Saint Petersburg Institute of Technology (Technical University), Moskovskiy pr. 26, 190013 Saint Petersburg, Russia;3. Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg 194021, Russia;1. Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran;2. Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan 45137-66731, Iran;3. DICATECh, Politecnico di Bari, I-70125 Bari, Italy;4. Shiraz Institute for Cancer Research, School of Medicine, Shiraz University of Medical Sciences, Shiraz, Iran;1. Department of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, Pajoohesh Blvd., km 17, Karaj Hwy, Tehran 14968-13151, Iran;2. Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35032 Marburg, Germany |
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| Abstract: | Heating cyclohexene at 70 °C in the presence of AcOH, t-BuOOH and catalytic amounts of both copper- acetate or -oxide and inexpensive commercial L-amino acids led to preferential formation of (S)-acetylcyclohexene. Up to ca. 30% enantiomeric excess has been attained by this procedure, which directly introduces an optically active center in an allylic position. |
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