Palladium-Catalyzed Asymmetric [4+3] Cyclization of Trimethylenemethane: Regio-, Diastereo-, and Enantioselective Construction of Benzofuro[3,2-b]azepine Skeletons |
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| Authors: | Dr Yang-Zi Liu Zhongao Wang Zesheng Huang Dr Xing Zheng Dr Wu-Lin Yang Prof Dr Wei-Ping Deng |
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| Institution: | School of Pharmacy and Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 P. R. China |
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| Abstract: | The palladium-catalyzed asymmetric 4+3] cyclization of trimethylenemethane donors with benzofuran-derived azadienes furnishes chiral benzofuro3,2-b]azepine frameworks in high yields (up to 98 %) with exclusive regioselectivities and excellent stereoselectivities (up to >20:1 d.r., >99 % ee). This catalytic asymmetric 4+3] cyclization of Pd-trimethylenemethane can enrich the arsenal of Pd-TMM reactions in organic synthesis. In addition, this strategy provides an alternative approach to chiral azepines by a transition-metal-catalyzed asymmetric 4+3] cyclization. |
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| Keywords: | [4+3]-Cyclisierung Asymmetrische Katalyse Chirale Azepine Cycloaddition Palladium |
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