6533b861fe1ef96bd12c45c0

RESEARCH PRODUCT

One-Pot Synthesis of Polysubstituted Pyrrolidines from Aminonitriles

Nino MeyerTill OpatzFrank Werner

subject

Group (periodic table)ChemistryOrganic ChemistryOne-pot synthesisOrganic chemistryGeneral MedicinePyrrole derivativesCatalysisCarbanion

description

α-Aminonitriles with a mono- or unsubstituted amino group as well as a-(alkylideneamino)nitriles can be employed as easily accessible α-aminocarbanion equivalents. Their α-deprotonation yields stabilized carbanions, whichundergo smooth 1,4-addition to α,β-unsaturated carbonyl compounds. The resulting δ-ketoα-aminonitriles can be reductively cyclized to form polysubstituted pyrrolidines.

https://doi.org/10.1055/s-2005-861838