Published in
MDPI, Molecules, 12(17), p. 14531-14554, 2012
DOI: 10.3390/molecules171214531
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Tandem RCM-Claisen Rearrangement-[2+2] Cycloaddition of O,O '-(But-2-en-1,4-diyl)-bridged Binaphthols
Journal article published in 2012 by
Michael Abraham,
Wolfgang Reischl,
Karl A. Kirchner 
,
Alexander Roller,
Luis F. Veiros ,
Michael Widhalm
,
Alexander Roller,
Luis F. Veiros ,
Michael Widhalm
This paper is made freely available by the publisher.
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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.