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

Angewandte ChemieVolume 125, Issue 16 p. 4562-4565 Zuschrift Enantioselective Synthesis of 2,2-Disubstituted Tetrahydrofurans: Palladium-Catalyzed [3+2] Cycloadditions of Trimethylenemethane with Ketones† Prof. Barry M. Trost, Corresponding Author Prof. Barry M. Trost [email protected] Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA)Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA)===Search for more papers by this authorDr. Dustin A. Bringley, Dr. Dustin A. Bringley Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA)Search for more papers by this author Prof. Barry M. Trost, Corresponding Author Prof. Barry M. Trost [email protected] Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA)Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA)===Search for more papers by this authorDr. Dustin A. Bringley, Dr. Dustin A. Bringley Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA)Search for more papers by this author First published: 12 March 2013 https://doi.org/10.1002/ange.201300616Citations: 14 † 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. Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract 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. Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. 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