RESUMO
Palladium(II)-catalyzed carboxylation of chiral olefins 6a-d has been examined under various conditions. In the weak basic condition (K2CO3), 7a-d were obtained in good yields. Alternatively, in the strong basic condition, pyrrolidinones 8a-d were obtained resulting in excellent yields and with high diastereoselectivity.
Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Pirrolidinonas/síntese química , Pirrolidinonas/farmacologia , Alcenos/química , Catálise , Cromatografia em Gel , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Paládio/química , Solventes , EstereoisomerismoRESUMO
In this study, a highly diastereoselective synthesis of anti-1,2-aminoalcohol was explored starting from L-amino acids as chiral sources. The higher yield and diastereoselectivity was shown when the aza-Claisen rearrangement was performed with allylic trichloroacetimidate 6a in the presence of palladium(II) catalyst.
Assuntos
Amino Álcoois/síntese química , Compostos Aza/química , Paládio/química , Catálise , Hidroxilação , Indicadores e Reagentes , EstereoisomerismoRESUMO
Stereoselective syntheses of (+/-)-epibatidine analogues 2, which contain the 8-azabicyclo [3.2.1]octane ring system, were achieved by using palladium-catalyzed cross-coupling reaction from 4 and the analgesic activity was tested by Mouse writhing antinociceptive assay.
Assuntos
Analgésicos não Narcóticos/síntese química , Compostos Bicíclicos Heterocíclicos com Pontes/síntese química , Agonistas Nicotínicos/síntese química , Piridinas/síntese química , Analgésicos não Narcóticos/química , Animais , Compostos Bicíclicos Heterocíclicos com Pontes/química , Catálise , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Masculino , Camundongos , Camundongos Endogâmicos ICR , Agonistas Nicotínicos/química , Medição da Dor/efeitos dos fármacos , Piridinas/química , EstereoisomerismoRESUMO
Syntheses of (+/-)-homoepibatidine analogues (2), which contain the 8-azabicyclo [3.2.1]octane ring system, were achieved by using palladium-catalyzed reductive-coupling reaction from 3 and the analgesic activity was tested by Mouse writhing antinociceptive assay.
