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Recent Developments in the Reformatsky-Claisen Rearrangement
Molecules 2012, 17(12), 14531-14554; doi:10.3390/molecules171214531
Article

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

1
, 1
, 2
, 3
, 4
 and 1,*
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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