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Enantioselective Synthesis of Highly Functionalized 4‐Piperidones by the Asymmetric Imino‐Diels–Alder Reaction of Chiral 2‐Amino‐1,3‐Butadienes
Author(s) -
Barluenga José,
Aznar Fernando,
Ribas Cristina,
Valdés Carlos,
Fernández Monica,
Cabal MaríaPaz,
Trujillo Jesús
Publication year - 1996
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19960020712
Subject(s) - enantioselective synthesis , diels–alder reaction , chemistry , organic chemistry , combinatorial chemistry , catalysis , stereochemistry
Chiral 2‐amino‐1,3‐butadienes 1 derived from commercially available ( S )‐2‐methoxymethylpyrrolidine react with aromatic N ‐trimethylsilylaldimines and N ‐phenylaldimines in the presence of ZnCl 2 to give, after the reaction workup, 4‐piperidones 4 and 6 , respectively, with moderate to very high enantiomeric excesses. In addition, the absolute configurations of derivatives of 4 a and 4 g were determined by circular dichroism and NMR spectroscopy on the Mosher ester, respectively.