Stereoselective Lewis acid promoted Kharasch-type addition of 3-bromoacetyl-2-oxazolidinones to norbornadiene |
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| Institution: | 1. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria;2. CL of Mineralogy and Crystallography, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria;1. State Key Laboratory of Geohazard Prevention and Geoenvironment Protection (Chengdu University of Technology), Chengdu University of Technology, College of Materials, Chemistry & Chemical Engineering, 1#, Dongsanlu, Erxianqiao, Chengdu 610059, Sichuan, PR China;2. Chengdu University of Technology, College of Environment and Ecology, 1#, Dongsanlu, Erxianqiao, Chengdu 610059, Sichuan, PR China;1. Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China;2. Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China |
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| Abstract: | Ytterbium trifluoromethanesulfonate promoted radical atom-transfer addition of 3-bromoacetyl-2-oxazolidinones to norbornadiene afforded stereoselectively the corresponding 5-exo-3-bromo-5-nortricycleneacetic acid derivatives in good yields. Following clean tri(trimethylsilyl)silane reduction of the bromides, 3-exo-nortricycleneacetic acid derivatives were obtained with excellent diastereoselectivities (90–96% de) when using the chiral 4-isopropyl- and 4-benzyl-substituted 2-oxazolidinone auxiliaries. The stereochemistry of the studied compounds was investigated by 1D and 2D NMR spectroscopy. |
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