Enantioselective synthesis of gamma-aryl-gamma-butyrolactones by sequential asymmetric epoxidation, ring expansion, and Baeyer-Villiger oxidation.
This paper describes an enantioselective synthesis of gamma-butyrolactones, using the N-tolyl-substituted oxazolidinone-containing ketone as catalyst and Oxone as oxidant via a sequential asymmetric epoxidation of benzylidenecyclopropanes, ring expansion, and Baeyer-Villiger oxidation. Up to 91% ee was obtained. Optically active cyclobutanones can also be obtained by suppressing the Baeyer-Villiger oxidation with use of more ketone catalyst and less Oxone.
Wang
Bin
B
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Shen
Yu-Mei
YM
Shi
Yian
Y
D015107:4-Butyrolactone / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D004852:Epoxy Compounds; D015107:4-Butyrolactone