tandem rcm–claisen rearrangement–[2+2] cycloaddition of o,o-(but-2-en-1,4-diyl)-bridged binaphthols串联rcm-claisen重排-[2 + 2]环加成反应的o,ou2019u2014u2014(but-2-en-1 4-diyl)桥接binaphthols.pdfVIP

Molecules 2012, 17, 14531-14554; doi:10.3390/molecules171214531 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O-(But-2-en-1,4-diyl)-bridged Binaphthols 1 1 2 3 4 Michael Abraham , Wolfgang Reischl , Karl A. Kirchner , Alexander Roller , Luis F. Veiros and Michael Widhalm 1,* 1 Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090 Wien, Austria; E-Mails: abraham350@ (M.A.); wolfgang.reischl@univie.ac.at (W.R.) 2 Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163/AC, A-1060 Wien, Austria; E-Mail: karl.kirchner@tuwien.ac.at 3 Faculty of Chemistry, Institute of Inorganic Chemistry, University of Vienna, Währinger Straße 42, A-1090 Wien, Austria; E-Mail: alexander.roller@univie.ac.at 4 Centro de Química Estrutural, Instituto Superior Técnico, Universidade Técnica de Lisboa, 1049-001 Lisboa, Portugal; E-Mail: veiros@ist.utl.pt * Author to whom correspondence should be addressed; E-Mail: m.widhalm@univie.ac.at; Tel.: +43-1-4277-52111; Fax: +43-1-4277-9521. Received: 30 October 2012; in revised form: 29 November 2012 / Accepted: 3 December 2012 / Published: 7 December 2012 Abstract: Attempted RCM of 2,2-bis(allyloxy)-1,1-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed