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Enantioseparation of secondary alcohols by diastereoisomeric salt formation
Author(s) -
Kiss Violetta,
Egri Gabriella,
Bálint József,
Fogassy Elemér
Publication year - 2005
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.20226
Subject(s) - chemistry , enantiomer , maleic acid , salt (chemistry) , alcohol , cinchonidine , chirality (physics) , enantiomeric excess , diastereomer , organic chemistry , medicinal chemistry , catalysis , enantioselective synthesis , copolymer , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model , polymer
A general method was found for the resolution of the racemic 1‐phenyl‐1‐propanol ( 1 ) and 1‐phenyl‐2‐propanol ( 2 ) with various resolving agents. Monoesters of the alcohols were prepared, which were then reacted with different chiral bases. Successful optical resolutions were achieved only with the maleic acid monoesters ( 3 and 6 ). Alcohol 1 has been resolved to >99% enantiomeric excess by diastereoisomeric salt formation via its maleic acid monoester ( 3 ) using cinchonidine ( 9 ) as resolving agent. Alcohol 2 has been obtained in 98% enantiomeric excess by diastereoisomeric salt formation via its the maleic acid monoester ( 6 ) using (+)‐dehydroabietylamine ( 11 ) as resolving agent. © 2005 Wiley‐Liss, Inc. Chirality 18:116–120, 2006.