Regioselective hypervalent iodine-induced Favorskii rearrangement of 3-oxo-5β-steroids.
Treatment of 3-oxo-5β-steroids with diacetoxyiodobenzene/KOH triggered a fast and regioselective Favorskii rearrangement that exclusively led to 3β-methoxycarbonyl-5β-4-norsteroids in good yields. The outcome of the reaction indicates that although both Cyclopropanone and Semi-benzylic pathways are possible, in the case of 3-oxo-5β-steroids, only the last participates. Unambiguous characterization of the products was achieved by NMR and X-ray Diffraction studies.
Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico.
Alejandro O
AO
Viviano-Posadas
Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico.
Marcos
M
Flores-Álamo
Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico. Electronic address: martin.iglesias@unam.mx.
Martín A
MA
Iglesias-Arteaga
D007455:Iodine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013256:Steroids / Q000737:chemistry*; D014961:X-Ray Diffraction
D013256:Steroids; D007455:Iodine
3-Oxo-5β-steroids; Favorskii rearrangement; Hypervalent iodine; NMR; Semi-benzylic mechanism; X-ray Diffraction