title: Studies on the BF3·Et2O catalyzed Baeyer-Villiger reaction of spiroketalic steroidal ketones.
abstract: During reactions of 23-oxosapogenins and the corresponding isomeric 22-oxo-23-spiroketals with MCPBA in the presence of BF(3)·Et(2)O, equilibration occurs between the ketones. The Baeyer-Villiger type oxidation is followed by fragmentation to the dinorcholanic lactones and 3-methylbutyrolactone. The mechanistic aspects of these reactions in the 25R and 25S series are discussed.
authors.affiliation: Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, México, DF, Mexico.
authors.forename: Mariana
authors.initials: M
authors.lastname: Macias-Alonso
authors.forename: Jacek W
authors.initials: JW
authors.lastname: Morzycki
authors.forename: Martin A
authors.initials: MA
authors.lastname: Iglesias-Arteaga
mesh_terms: D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D010084:Oxidation-Reduction; D012502:Sapogenins / Q000737:chemistry; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*
chemical_list: D001880:Boranes; D007659:Ketones; D012502:Sapogenins; D013256:Steroids; C101707:boron trifluoride etherate