Enantioselective Synthesis of 3,3-Disubstituted Piperidine Derivatives by Enolate Dialkylation of Phenylglycinol-Derived Oxazolopiperidone Lactams
The Journal of Organic Chemistry2007Vol. 72(12), pp. 4431–4439
Citations Over TimeTop 10% of 2007 papers
Abstract
The stereochemical outcome of the enolate dialkylation of simple phenylglycinol-derived oxazolopiperidone lactams is studied. High stereoselectivities in the generation of the quaternary stereocenter are obtained by the appropriate choice of both the configuration of the starting lactam and the order of introduction of the substituents. The usefulness of the methodology is illustrated by the conversion of some of the dialkylated lactams into known synthetic precursors of alkaloids and by the total synthesis of (-)-quebrachamine.
Related Papers
- → Enantioselective synthesis of spirooxoindoles via chiral auxiliary (bicyclic lactam) controlled SNAr reactions(2010)30 cited
- → Enantioselective Divergent Syntheses of Cephalotaxus Alkaloids: (−)-Cephalotaxine, (−)-Cephalotine B, and (−)-Fortuneicyclidins A and B(2023)24 cited
- → Enantioselective Total Synthesis of (−)-Misramine(2018)17 cited
- → Asymmetric Intramolecular Carbolithiation of Achiral Substrates: Synthesis of Enantioenriched (R)-(+)-Cuparene and (R)-(+)-Herbertene(2014)13 cited
- → Synthetic studies towards the octahydro-1H-benzo[f]pyrrolo[3,2,1-ij]quinolines: enantioselective synthesis of (2R,3S)-2-[(1S)-3-(benzyloxy)-1-(tert-butyldimethyl-silyloxymethyl)propyl]-3-phenylhexahydropyridine(2001)6 cited