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Totally Regio- and Stereoselective Behavior of Mono- and Diactivated Cyclic Alkenes in the Lu Reaction: Synthesis of Enantiopure Functionalized Cyclopentanes

Author/s
García Ruano, J. L.; Nuñez Jr., A.; Martín, M. R.; Fraile, A.
Año de edición
2008
Referencia completa

J. Org. Chem. 2008, 73, 9366-9371. DOI: 10.1021/jo801896a

Resumen

5-Alkoxyfuran-2(5H)-ones and their optically pure 3-p-tolylsulfinyl derivatives, synthetic equivalents of the acyclic esters, react with dipoles generated from allenoates and PPh3 (Lu reaction), in a completely regioselective, π-facial selective and endo-selective manner, yielding bicyclic adducts, which are easily converted into optically pure highly substituted cyclopentane derivatives.

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