Asymmetric Synthesis of Highly Substituted Pyrrolidines by 1,3‐Dipolar Cycloadditions of Azomethine Ylides with  N ‐Acryloylproline Benzyl Ester | Zendy

Waldmann Herbert | Zendy; Bläser Edwin | Zendy; Jansen Martin | Zendy; Letschert HansPeter | Zendy

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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.

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