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Crystallization‐Induced Asymmetric Transformations. Enantiomerically pure (−)‐( R )‐ and (+)‐( S )‐2,3‐Dibromopropan‐1‐ol and Epibromohydrins. A Study of Dynamic Resolution via the Formation of Diastereoisomeric Esters
Author(s) -
Brunetto Gabriella,
Gori Susanna,
Fiaschi Rita,
Napolitano Elio
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200211)85:11<3785::aid-hlca3785>3.0.co;2-a
Subject(s) - chemistry , enantiomer , crystallization , transesterification , racemization , resolution (logic) , diastereomer , biphenyl , enantioselective synthesis , alcohol , organic chemistry , stereochemistry , medicinal chemistry , catalysis , artificial intelligence , computer science
Abstract ( S )‐2,3‐Dibromopropan‐1‐ol of high enantiomer excess was obtained by crystallization‐induced asymmetric transformations of racemic 2,3‐dibromopropan‐1‐ol esterified with N ‐([1,1′‐biphenyl]‐4‐ylcarbonyl‐ L ‐alanine; in particular, an asymmetric transformation of the first type (involving bromide exchange to equilibrate the diastereoisomeric esters) and an asymmetric transformation of the second type (involving a transesterification of diastereoisomeric esters with excess racemic alcohol) were devised.