Premium
Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids
Author(s) -
Nyhlén Jonas,
Eriksson Lars,
Bäckvall JanE.
Publication year - 2008
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.20479
Subject(s) - cinchonidine , diastereomer , chemistry , cinchonine , enantiomer , resolution (logic) , salt (chemistry) , enantiomeric excess , absolute configuration , chiral resolution , yield (engineering) , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , materials science , artificial intelligence , computer science , metallurgy
A synthetic procedure for the preparation of 4‐cyclohexyl‐2‐methyl‐buta‐2,3‐dienoic acid in the two optically active forms has been developed. Synthesis of the racemic allenoic acid was made by an efficient route with good overall yield. Resolution of the enantiomers was achieved by forming the cinchonidine and cinchonine diastereomeric salt, respectively, and the enantiomers were isolated in up to 95% enantiomeric excess. The absolute configuration of the allenoic acid was determined by X‐ray crystallography. Chirality, 2007. © 2007 Wiley‐Liss, Inc.