Efficient asymmetric selenocyclizations of alkenyl oximes into cyclic nitrones and 1,2-oxazines promoted by sulfur containing diselenides |
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Institution: | 1. State Key Laboratory of Bioreactor Engineering, New World Institute of Biotechnology, East China University of Science and Technology, Shanghai 200237, PR China;2. Enzyme and Fermentation Technology Laboratory, College of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing 210037, PR China |
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Abstract: | Treatment of the di-2-(1S)-1-(methylthio)ethyl]phenyl diselenide or of the di-2-methoxy-6-(1S)-1-methylthio)ethyl]phenyl diselenide with bromine and silver triflate afforded the corresponding electrophilic selenylating triflates which were used in situ to promote the asymmetric selenocyclization of γ-alkenyl oximes and δ-phenyl-γ-alkenyl oximes. The course of these reactions and hence the structures of the cyclization products were dictated by the (E)- or (Z)-geometry of the starting oximes. The two types of cyclization products were either the cyclic nitrones or the 1,2-oxazines; in both cases the reactions proceeded with excellent yields, complete regioselectivity and good diastereoselectivity. |
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