Asymmetric synthesis of hydroxylated pyrrolizidine, indolizidine, and (+)-alpha-conhydrine via ruthenium-catalyzed hydrogenation.
The enantioselective ruthenium promoted hydrogenation of beta-keto ester, derived from (S)- or (R)-proline and (S)-pipecolic acid, provided a new efficient route to hydroxylated pyrrolizidine or indolizidine ring systems in diastereomeric excesses up to 99%. A practical synthesis of (+)-alpha-conhydrine is also reported.
Guerreiro
P
P
Laboratoire de Synthese Selective Organique et Produits Naturels, Paris, France.
Ratovelomanana-Vidal
V
V
Genet
J P
JP
D000470:Alkaloids / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D002621:Chemistry / Q000379:methods*; D006859:Hydrogen / Q000378:metabolism*; D007212:Indolizines / Q000138:chemical synthesis*; D008956:Models, Chemical; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry*
D000470:Alkaloids; D000596:Amino Acids; D007212:Indolizines; D011763:Pyrrolizidine Alkaloids; D012428:Ruthenium; D006859:Hydrogen