γ-Amino alcohols via organocascade reactions involving dienamine catalysis

Chandrakumar Appayee, Americo J. Fraboni, Stacey E. Brenner-Moyer

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

Whereas cascade reactions catalyzed by secondary amines combine iminium- and/or enamine-catalyzed reactions, we introduce the feasibility of combining these modes of catalysis with dienamine-catalysis as a new general mechanism for cascade reactions. Enantioenriched β-functionalized-γ-amino alcohols were produced from simple achiral enals in one flask by combining dienamine- and iminium-catalyzed intermolecular reactions. Reaction products are precursors of γ-amino acids, γ-lactams, and pyrrolidines; one was employed in a synthesis of γ-amino acid (S)-vigabatrin, the bioactive enantiomer of Sabril.

Original languageEnglish (US)
Pages (from-to)8828-8834
Number of pages7
JournalJournal of Organic Chemistry
Volume77
Issue number19
DOIs
Publication statusPublished - Oct 5 2012
Externally publishedYes

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this