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Enantioselective Synthesis of 2,2-Disubstituted Tetrahydrofurans: Palladium-Catalyzed [3+2] Cycloadditions of Trimethylenemethane with Ketones

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  • We thank the NSF (CHE-1145236) and the NIH (GM 033049) for their generous support of our programs. Additional financial support was provided by the W. S. Johnson Graduate Fellowship (D.A.B.). Palladium salts were a generous gift from Johnson Matthey. We thank Dr. Allen Oliver at the University of Notre Dame for X-ray crystal analyses.

Abstract

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O-Ringe: Die Cycloaddition von Trimethylenmethan an Arylketone liefert die Titelverbindungen in bis zu 96 % Ausbeute und 95 % ee. Der palladiumkatalysierte Prozess nutzt den Liganden L1 mit einem stereogenen Phosphorzentrum, wobei nur eines der Epimere bezüglich dieses Phosphorzentrums den aktiven Katalysator ergibt. Cp=Cyclopentadien, TMS=Trimethylsilyl.

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