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A Practical Asymmetric Synthesis of Enantiomerically Pure 3‐Substituted Pyroglutamic Acids and Related Compounds
Author(s) -
Soloshonok Vadim A.,
Cai Chaozhong,
Hruby Victor J.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000616)39:12<2172::aid-anie2172>3.0.co;2-0
Subject(s) - pyroglutamic acid , stereoselectivity , alkyl , chemistry , glycine , aryl , stereochemistry , amino acid , organic chemistry , catalysis , biochemistry
DBU‐catalyzed Michael addition reactions were shown to occur at room temperature between a nickel( II ) complex of the Schiff base of glycine 1 and ( S )‐ or ( R )‐ N ‐( E ‐enoyl)‐4‐phenyl‐3‐oxazolidin‐2‐ones ( 2 , see scheme). This reaction, which has an almost completely stereoselective outcome, provides a practical and generalized approach to a family of glutamic/pyroglutamic acids. R=alkyl, aryl.