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Angewandte Chemie DOI: 10.1002/anie.201207405 Carbocycles Catalytic [4+2] Cyclization of a,b-Unsaturated Acyl Chlorides with 3-Alkylenyloxindoles: Highly Diastereo- and Enantioselective Synthesis of Spirocarbocyclic Oxindoles** Li-Tao Shen, Wen-Qiang Jia, and Song Ye* The spirooxindole is a privileged structure moiety found in many biologically active natural products and pharmaceuti- cally active compounds.[1] Thus, many elegant approaches have been developed for its construction.[2] Typical intra- molecular approaches are the oxidative rearrangement of tetrahydro-b-carbolines,[3] and the palladium-catalyzed Heck reaction.[4] The intermolecular cyclization, which forms two or more CC bonds in one pot, is very interesting for the construction of cyclic compounds, because it is a step- economic approach and the starting materials are relatively readily available.[5] Trost and co-workers reported a palla- dium-catalyzed [3+2] cyclization of 3-alkenyloxindole with trimethylenemethane, leading to the spirocyclic oxindolic cyclopentanes in good yields with high enantioselectivities.[6] Scheme 1. Lewis base catalyzed cyclization of a,b-unsaturated acyl A facile synthesis of spirooxindole, developed by Carreira chlorides. and co-workers, involves the formal [3+2] cyclization of spirocyclopropane with aldimines.[7] Recently, several effi- cient routes