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.metzner
ensicaen.fr
M. Davoust, J.-F. Briere, P.-A. Jaffres, P. Metzner, J. Org. Chem., 2005, 70, 4166-4169.
DOI: 10.1021/jo0479260
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
