681179-33-9Relevant articles and documents
Baeyer–Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones
Rodríguez-Mata, María,Lavandera, Iván,Gotor-Fernández, Vicente,Gotor, Vicente,García-Cerrada, Susana,Mendiola, Javier,de Frutos, óscar,Collado, Iván
, p. 7268 - 7275 (2016/10/26)
A series of γ-butyrolactone derivatives, including some spiranic ones, was obtained through desymmetrization of the corresponding prochiral 3-substituted cyclobutanones via Baeyer–Villiger monooxygenase (BVMO)-catalyzed oxidation. After reaction optimization using several commercial enzymes, both antipodes of various lactones were synthesized in most cases with >90% conversion and >80% enantiomeric excess under mild reaction conditions. In some cases alcohol formation was also observed (up to 40% conversion) as an undesired side reaction due to the presence of alcohol dehydrogenases in these preparations. Selected transformations were achieved on a 100 mg scale showing the possibilities of these oxidative biocatalysts as a new source of highly interesting compounds.
Chemoenzymatic synthesis of enantioenriched 5-oxo-tetrahydro-3- furancarboxylic acid derivatives
Comini, Andrea,Forzato, Cristina,Nitti, Patrizia,Pitacco, Giuliana,Valentin, Ennio
, p. 617 - 625 (2007/10/03)
(R)-(+)-Paraconic acid 4, (S)-(-)-terebic acid 6 and their corresponding methyl and ethyl esters having ee's ranging from 60% to 92% were obtained by enzymatic resolution of their racemates. The enzymatic resolution of racemic ethyl γ-methylparaconates 14a and 14b allowed the isolation of the unreacted ester (2R,3R)-(+)-14a and that of the lactonic acid (2S,3R)-(-)-5b with 80% and 93% ee, respectively, the former by the use of Horse liver acetone powder (HLAP), the latter using α-chymotrypsin (α-CT). The enantiomeric ethyl (2S,3S)-(-)-14a and (2S,3R)-(-)-14b, both with >99% ee, were obtained by baker's yeast reduction of diethyl acetylsuccinate.
