The RhodiumCatalyzed Carbene Cyclization Cycloaddition Cascade Reaction of Vinylsulfonates

Autor: Shi, Bairu, Merten, Sandra, Wong, David K.Y., Chu, John C.K., Liu, Lok Lok, Lam, Sze Kui, Jäger, Anne, Wong, WingTak, Chiu, Pauline, Metz, Peter
Zdroj: Advanced Synthesis & Catalysis; December 2009, Vol. 351 Issue: 18 p3128-3132, 5p
Abstrakt: Vinylsulfonates have proved to be excellent dipolarophiles for carbonyl ylides derived from diazoketones in rhodiumcatalyzed intramolecular cycloadditions. Polyfunctional substrates, such as 8and 15, were readily available from hydroxy esters, e.g. 1and the cyclopenta1,3dione 10, respectively, and the resulting polycyclic sultones were formed under mild reaction conditions in high yields with very good diastereoselectivities. A rutheniumcatalyzed asymmetric transfer hydrogenation was found to desymmetrize the mesocyclopenta1,3dione 12efficiently.
Databáze: Supplemental Index