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Synthesis of Highly Functionalized Cyclooctenes by Ring‐Closing Metathesis: Unexpected Formation of a trans Isomer
Author(s) -
Bourgeois Damien,
Pancrazi Ange,
Ricard Louis,
Prunet Joëlle
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000218)39:4<725::aid-anie725>3.0.co;2-i
Subject(s) - metathesis , ring closing metathesis , salt metathesis reaction , derivative (finance) , chemistry , catalysis , combinatorial chemistry , ring (chemistry) , organic chemistry , polymerization , financial economics , economics , polymer
Grubbs' and Schrock's catalysts can be used in ring‐closing metathesis reactions (RCM) to synthesize highly functionalized cyclooctenes that have the required stereochemistry for the C1, C2, and C8 centers of taxol. The unprecedented formation of a trans isomer in the case of the carbonate derivative (see scheme) indicates that RCM does not always proceed to complete thermodynamic equilibrium.