Título
Synthesis of diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate by Pd-catalyzed intramolecular allylic alkylation. Stereoselective preparation of its optically homogeneous form from R-(−)-carvone
Autor(es)
Palabras clave
Allylic alkylation
Monoterpenes
Pd catalysis
Stereoselective synthesis
Fecha de publicación
2010
Editor
Elsevier
Citación
Galán-Fernández, R., Clemente-Tejeda, D., Río-Nieto, E. del, & Bermejo, F. A. (2010). Synthesis of diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate by Pd-catalyzed intramolecular allylic alkylation. Stereoselective preparation of its optically homogeneous form from R-(−)-carvone. Tetrahedron, 66(42), 8247–8253. https://doi.org/10.1016/j.tet.2010.08.051
Resumen
[EN]A new route to racemic diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6- dicarboxylate (±)-1a by means of a palladium-catalyzed intramolecular allylic alkylation exercised on malonate-ester derivatives has been developed from R-(-)-carvone. The stereocontrolled synthesis of the enantiomerically pure (-)-1b by application of a six-step reactions sequence with a 28% overall yield from acetal 8, has been accomplished.
URI
ISSN
0040-4020
DOI
10.1016/j.tet.2010.08.051
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