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Design of Sulfides with a Locked Conformation as Promoters of Catalytic and Asymmetric Sulfonium Ylide Epoxidation

Marion Davoust, Jean-François Brière, Paul-Alain Jaffrès and Patrick Metzner*

*Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ENSICaen-Université de Caen, 6 Boulevard du Maréchal Juin, 14050 Caen, France, Email: patrick.metznerensicaen.fr

M. Davoust, J.-F. Briere, P.-A. Jaffres, P. Metzner, J. Org. Chem., 2005, 70, 4166-4169.

DOI: 10.1021/jo0479260 (free Supporting Information)


Abstract

The asymmetric addition of chiral sulfonium ylides to aldehydes is promoted by 2,5-dimethylthiolanes with a locked conformation. This user-friendly organocatalytic process proved to be efficient with 20-10% of sulfide in 1 or 2 days of reaction.

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Key Words

Sulfonium Ylide, Epoxides, Corey-Chaykovsky Reaction, Organocatalysis


ID: J42-Y2005-500