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Synfacts 2006(3): 0213-0213  
DOI: 10.1055/s-2006-931975
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of P-Stereogenic Oxaphosphacyclohexene-1-oxides by Ring-Closing Metathesis

Contributor(s): Victor Snieckus, Farhad Nowrouzi
K. S. Dunne, F. Bisaro, B. Odell, J.-M. Paris, V. Gouverneur*
University of Oxford, UK and Rhodia Recherches, Saint-fons, France
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

The synthesis of P-stereogenic oxaphosphacyclohexene-1-oxides by Ru(II)-catalyzed diastereoselective ring-closing metathesis of prochiral phosphorus trienes is reported. The reaction proceeds in good to excellent yields under mild conditions, with poor to good level of diastereocontrol and without formation of products resulting from intermolecular cross-metathesis. In terms of substituent effects, the observed 1,3-­diastereoinduction is superior to that of 1,4-dia­stereoinduction.