Collect. Czech. Chem. Commun.
2005, 70, 1953-1969
https://doi.org/10.1135/cccc20051953
Sulfoxide-Modified Julia-Lythgoe Olefination: Highly Stereoselective Di-, Tri-, and Tetrasubstituted Double Bond Formation
Jiří Pospíšil, Tomáš Pospíšil and István E. Markó*
Département de Chimie, Université catholique de Louvain, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium
Abstract
A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and SmI2/HMPA or SmI2/DMPU-mediated reductive elimination, 1,2-di-, tri- and tetrasubstituted olefins in moderate to good yields and E/Z selectivity. The conditions are mild and the procedure is widely applicable. The reaction mechanism was studied and a general model, describing the reaction selectivity, is proposed.
Keywords: Olefinations; Samarium; Reaction mechanisms; Additions; Synthetic methods; Julia-Lythgoe olefination; Sulfoxides; Alkenes; Reductive elimination.
References: 40 live references.
