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Olefin Metathesis: A Reversible Stimulus for a Conformational Switch
Author(s) -
Garcia M.Elisa Juarez,
Fröhlich Ute,
Koert Ulrich
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700068
Subject(s) - chemistry , decalin , olefin metathesis , ring closing metathesis , ring (chemistry) , ring size , stereochemistry , metathesis , salt metathesis reaction , organic chemistry , catalysis , polymerization , polymer
A ring‐closing olefin metathesis (RCM) to an eight‐membered ring is suitable to induce a conformational switch of a 2,3,6,7‐tetrasubstituted cis ‐decalin. The double‐ring flip of the decalin scaffold can be reversed by a ring‐opening metathesis. The corresponding RCM to a 14‐membered ring does not force the double ring flip to occur. A ring‐size competition experiment resulted in the exclusive formation of an eight‐membered ring. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)