TY - JOUR
T1 - γ-Amino alcohols via organocascade reactions involving dienamine catalysis
AU - Appayee, Chandrakumar
AU - Fraboni, Americo J.
AU - Brenner-Moyer, Stacey E.
PY - 2012/10/5
Y1 - 2012/10/5
N2 - 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.
AB - 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.
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U2 - 10.1021/jo3017007
DO - 10.1021/jo3017007
M3 - Article
C2 - 22970912
AN - SCOPUS:84867362571
SN - 0022-3263
VL - 77
SP - 8828
EP - 8834
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -