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Darstellung der enantiomeren erythro ‐ und threo ‐1,2,3‐Pentantriole mit Hilfe einer enzymatischen Racematspaltung
Author(s) -
Claßen Arnold,
Wershofen Stefan,
Yusufoĝlu Ayse,
Scharf HansDieter
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870710
Subject(s) - chemistry , diastereomer , enantiomer , stereochemistry , resolution (logic) , regioselectivity , lipase , ring (chemistry) , enzyme , catalysis , organic chemistry , artificial intelligence , computer science
Preparation of Enantiomeric erythro ‐ and threo ‐1,2,3‐Pentanetriols by an Enzymatic Recemate Resolution (2 R ,3 S )‐ and (2 S ,3 R )‐ erythro ‐ ( 9a/9b ) as well as (2 R ,3 R )‐ and (2 S ,3 S )‐ threo ‐1,2,3‐pentanetriol ( 10a/10b ) are synthesized from the rac. trans ‐ and cis ‐isomeric 2,3‐epoxypentyl butyrates 5/6 by Lipase‐controled racemate resolution followed by regioselective ring opening of both the chiral epoxy alcohols 3a/3b and 4a/4b , respectively. Whereas the erythro ‐triols 9a and 9b are obtained in very good enantiomeric excesses, the reaction sequence yields poor ee values in the case of the threo ‐triols 10a and 10b .