Castelló Moncayo, Luis Miguel, Selva, Verónica, Nájera, Carmen, Sansano, Jose M.
Multicomponent Diastereoselective Synthesis of Indolizidines via 1,3-Dipolar Cycloadditions of Azomethine Ylides
Synthesis. 2017, 49(02): 299-309. doi:10.1055/s-0036-1588620
URI: http://hdl.handle.net/10045/61487
DOI: 10.1055/s-0036-1588620
ISSN: 0039-7881 (Print)
Abstract: 
The synthesis of polyfunctionalized indolizidines from pipecolinic acid alkyl ester derivatives, aldehydes and a wide range of dipolarophiles by multicomponent 1,3-dipolar cycloadditions is developed in a diastereoselective manner. The cycloadditions take place in toluene with short reaction times at 70 °C, giving good yields. The synthesis of these fused heterocycles is also studied starting from pipecolinic acid, generating the dipole through a decarboxylative route at 120 °C. The relative configuration of the resulting products as well as the mechanistic pathways are also explained.
Keywords:Cycloaddition, Multicomponent, Indolizidines, Azomethine ylides, Iminium route, Decarboxylative route
Georg Thieme Verlag
info:eu-repo/semantics/article