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Prof. Barry M. Trost and Dr. Dustin A. Bringley Enantioselective Synthesis of 2,2-Disubstituted Tetrahydrofurans: Palladium-Catalyzed [3+2] Cycloadditions of Trimethylenemethane with Ketones Angewandte Chemie International Edition 52

Version of Record online: 12 MAR 2013 | DOI: 10.1002/anie.201300616

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O rings: An approach to the title compounds has been developed utilizing a cycloaddition of trimethylenemethane with aryl ketones. The products are formed in up to a 96 % yield with 95 % ee. The reaction is catalyzed by palladium in the presence of L1, which possesses a stereogenic phosphorus atom, and only a single epimer at the phosphorus atom yields the active catalyst. Cp=cyclopentadiene, TMS=trimethylsilyl.

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