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

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

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,...

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Veröffentlicht in:Journal of organic chemistry 2008-12, Vol.73 (23), p.9366-9371
Hauptverfasser: García Ruano, José L, Núñez, Jr, Alberto, Rosario Martín, M, Fraile, Alberto
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801896a