Synthesis of highly functionalized cyclooctenes by ring-closing metathesis: Unexpected formation of a trans isomer

Damien Bourgeois (1) , A. Pancrazi (2) , Louis Ricard (3) , Joëlle Prunet (1)

1 DCSO - Laboratoire de synthèse organique
2 Laboratoire de Synthèse Organique Sélective et Chimiie Organométallique
3 DCPH - Laboratoire Hétéroéléments et Coordination

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.

Domains: Chemical Sciences; Organic chemistry

Damien Bourgeois, A. Pancrazi, Louis Ricard, Joëlle Prunet. Synthesis of highly functionalized cyclooctenes by ring-closing metathesis: Unexpected formation of a trans isomer. Angewandte Chemie International Edition, 2000, 39 (4), pp.725-728. ⟨10.1002/(SICI)1521-3773(20000218)39:4<725::AID-ANIE725>3.0.CO;2-I⟩. ⟨hal-00954912⟩