Premium
Preparative Scale Directed Resolution of Enantiomeric Carboxylic Acids and Lactones via Liquid Chromatography and Neighboring‐Group Assisted Hydrolysis of Diastereomeric Amides
Author(s) -
Helmchen Günter,
Nill Günter,
Flockerzi Dieter,
Youssef Mohamed S. K.
Publication year - 1979
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.197900631
Subject(s) - diastereomer , chemistry , enantiomer , hydrolysis , resolution (logic) , carboxylic acid , chromatography , organic chemistry , silica gel , artificial intelligence , computer science
The separation of enantiomeric carboxylic acids (1) on a preparative scale (1 mol) can be accomplished by the following reaction sequence: transformation of (1) with optically active amines, e.g. (2) , containing polar groups, into diastereomeric amides → separation of the amides by liquid chromatography on silica gel columns → mild acidic hydrolysis. Amines such as (3) without additional polar groups suffice for separation of lactones.