γ-Amino alcohols via organocascade reactions involving dienamine catalysis.
J Org Chem
; 77(19): 8828-34, 2012 Oct 05.
Article
em En
| MEDLINE
| ID: mdl-22970912
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 ß-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.
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MEDLINE
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En
Ano de publicação:
2012
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Article