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A New Route to Enantiopure β‐Aryl‐Substituted β‐Amino Acids and 4‐Aryl‐Substituted β‐Lactams through Lipase‐Catalyzed Enantioselective Ring Cleavage of β‐Lactams
Author(s) -
Forró Enikő,
Paál Tihamér,
Tasnádi Gábor,
Fülöp Ferenc
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505434
Subject(s) - enantiopure drug , enantioselective synthesis , chemistry , aryl , enantiomer , candida antarctica , cleavage (geology) , ring (chemistry) , stereochemistry , catalysis , enantiomeric excess , lactam , lipase , amino acid , organic chemistry , enzyme , biochemistry , alkyl , geotechnical engineering , fracture (geology) , engineering
A simple and efficient direct enzymatic method was developed for the synthesis of 4‐aryl‐substituted β‐lactams and the corresponding β‐amino acid enantiomers through the CAL‐B (lipase B from Candida antarctica )‐catalyzed enantioselective ( E >200) ring cleavage of the corresponding racemic β‐lactams with 1 equiv. of H 2 O in i‐ Pr 2 O at 60 °C. The product ( R )‐β‐amino acids (ee≥98%, yields≥42%) and unreacted ( S )‐β‐lactams (ee≥95%, yields≥41%) could be easily separated. The ring opening of enantiomeric β‐lactams with 18% HCl afforded the corresponding enantiopure β‐amino acid hydrochlorides (ee≥99%).