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Molecules 2012, 17(12), 14531-14554; doi:10.3390/molecules171214531

Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols

1
Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090 Wien, Austria
2
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163/AC, A-1060 Wien, Austria
3
Faculty of Chemistry, Institute of Inorganic Chemistry, University of Vienna, Währinger Straße 42, A-1090 Wien, Austria
4
Centro de Química Estrutural, Instituto Superior Técnico, Universidade Técnica de Lisboa, 1049-001 Lisboa, Portugal
*
Author to whom correspondence should be addressed.
Received: 30 October 2012 / Revised: 29 November 2012 / Accepted: 3 December 2012 / Published: 7 December 2012
(This article belongs to the Special Issue Claisen Rearrangement)
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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 by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided.
Keywords: DFT calculations; Grubbs II catalyst; cage compounds; spiro-compounds; chiral macrocycle DFT calculations; Grubbs II catalyst; cage compounds; spiro-compounds; chiral macrocycle
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MDPI and ACS Style

Abraham, M.; Reischl, W.; Kirchner, K.A.; Roller, A.; Veiros, L.F.; Widhalm, M. Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols. Molecules 2012, 17, 14531-14554.

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