6533b851fe1ef96bd12a8ca1

RESEARCH PRODUCT

Addition of α-Aminonitriles to α,β-Unsaturated Carbonyl Compounds: A One-Pot Synthesis of Polysubstituted Pyrrolidines.

Till OpatzNino Meyer

subject

chemistry.chemical_compoundDeprotonationchemistryReaction sequenceOne-pot synthesisSubstituentOrganic chemistryGeneral MedicinePyrrole derivativesCarbanion

description

The vinylogous addition of deprotonated N-alkyl-α-aminonitriles to α,β-unsaturated carbonyl compounds yields cyclic intermediates which can be reduced to form polysubstituted pyrrolidines in a one-pot reaction sequence. Since the cyano substituent is lost in the reduction step, the aminonitriles serve as easily accessible (N-alkylamino)-substituted carbanion equivalents.

https://doi.org/10.1002/chin.200349110