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Stereoisomeric flavour compounds LXVII. 2‐, 3‐, and 4‐Alkyl‐branched acids, part 1: General approach to the synthesis of the enantiopure acids
Author(s) -
Karl Volker,
Kaunzinger Astrid,
Gutser Jutta,
Steuer Petra,
AnglesAngel Jorge,
Mosandl Armin
Publication year - 1994
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530060510
Subject(s) - enantiopure drug , chemistry , diastereomer , alkyl , enantiomer , alkylation , organic chemistry , absolute configuration , enantiomeric excess , stereochemistry , enantioselective synthesis , catalysis
A general approach to the synthesis of 2‐, 3‐, and 4‐alkyl‐branched acids of high enantiomeric purity is described. The enantiopure 2‐alkyl‐branched acids are prepared via liquid chromatographic resolution of diastereomeric phenylglycinol amides and their absolute configuration is deduced from the 1 H‐NMR data of the separated diastereomers. Chain elongation methods, by Arndt–Eistert synthesis, via 2‐alkylated alkyl carbonitrile or by malonic ester synthesis, are used to prepare 3‐ and 4‐alkyl‐branched acids of high configurational purity and known absolute configuration starting from the enantiomeric 2‐alkyl‐branched acids. © 1994 Wiley‐Liss, Inc.