6533b835fe1ef96bd12a00ce
RESEARCH PRODUCT
N-sulfinyl amines as a nitrogen source in the asymmetric intramolecular aza-Michael reaction: total synthesis of (-)-pinidinol.
Carlos Del PozoSilvia MonteagudoSonia FloresMaría Sánchez-rosellóPablo BarrioSantos Fusterosubject
StereochemistryNitrogenStereoisomerismMedicinal chemistryCatalysisCatalysisStereocenteraza-Michael reactionchemistry.chemical_compoundNucleophilePiperidinespiperidinesAminesMolecular StructureChemistryOrganic ChemistryTotal synthesispyrrolidinesStereoisomerismGeneral ChemistrysullinylaminesIntramolecular forceSulfoxidesMichael reactioncross metathesisPiperidinedescription
N-Sulfinyl amines have been successfully employed as nitrogen nucleophiles for the asymmetric intramolecular aza-Michael reaction. The synthetic strategy involves a cross-metathesis reaction followed by the Michael-type cyclization, either in a base-catalyzed two-step procedure or in a tandem fashion. The developed methodology allows access to chiral substituted pyrrolidines and piperidines bearing one or two stereocenters and it has been applied to the synthesis of the piperidine alkaloid (-)-pinidinol.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-01-01 | Chemistry (Weinheim an der Bergstrasse, Germany) |