Sulfoxide-modified Julia-Lythgoe olefination: Highly stereoselective di-, tri-, and tetrasubstituted double bond formation
(2005) Collection of Czechoslovak Chemical Communications — Vol. 70, n° 11, p. 1953-1969 (2005)
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- 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.
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Pospisil, J., Pospisil, T., & Marko, I. (2005). Sulfoxide-modified Julia-Lythgoe olefination: Highly stereoselective di-, tri-, and tetrasubstituted double bond formation. Collection of Czechoslovak Chemical Communications, 70(11), 1953-1969. https://doi.org/10.1135/cccc20051953 (Original work published 2005)