BioChem - DOS

Baeyer-Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones

Tetrahedron

Rodriguez-Mata, M.; Lavandera, I.; Gotor-Fernandez, V.; Gotor, V.; Garcia-Cerrada, S.; Mendiola, J.; de Frutos, O.; Collado, I.

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.

2016

Pergamon Press

0040-4020

1464-5416

72

46

pp.7268-7275

10.1016/j.tet.2015.12.071

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART76628247

Asymmetric synthesis; Baeyer-Villiger oxidation; Lactones; Oxygenases; Spiro compounds