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Asymmetric Synthesis of Highly Substituted Pyrrolidines by 1,3‐Dipolar Cycloadditions of Azomethine Ylides with N ‐Acryloylproline Benzyl Ester
Author(s) -
Waldmann Herbert,
Bläser Edwin,
Jansen Martin,
Letschert HansPeter
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199406831
Subject(s) - chemistry , enantiomer , organic chemistry , proline , azomethine ylide , amino acid , 1,3 dipolar cycloaddition , medicinal chemistry , cycloaddition , catalysis , biochemistry
Azomethine ylides accessible from Schiff's bases of aliphatic and aromatic amino acid esters undergo asymmetric 1,3‐dipolar cycloadditions with N ‐acryloyl‐( S )‐proline benzyl ester in THF at low temperatures. Satisfactory yields of highly substituted pyrrolidines of type 1 are obtained in excellent enantiomeric excesses. The corresponding 2,4‐dicarboxylic acids can be readily prepared from these pyrrolidines. Bzl = benzyl.