Enantioseparation of secondary alcohols by diastereoisomeric salt formation | Zendy

Kiss Violetta | Zendy; Egri Gabriella | Zendy; Bálint József | Zendy; Fogassy Elemér | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research