Totally regio- and stereoselective behavior of mono- and diactivated cyclic alkenes in the Lu reaction: synthesis of enantiopure functionalized cyclopentanes |
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| Authors: | García Ruano José L Núñez Alberto Martín M Rosario Fraile Alberto |
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| Institution: | Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es |
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| Abstract: | 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 PPh(3) (Lu reaction), in a completely regioselective, pi-facial selective and endo-selective manner, yielding bicyclic adducts, which are easily converted into optically pure highly substituted cyclopentane derivatives. |
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