Stereospecific synthesis of highly functionalized tricyclic beta-lactams by radical cyclizations using titanocene monochloride.
The reductive opening of epoxyimonobactams 1 with titanoncene (III) chloride gives rise to radicals that can be trapped by intramolecular pi systems (i.e., conjugated alkenes and lactone and amide carbonyls) in a stereospecific way to give new carbocyclic compounds such as tribactam 2.
Ruano
Gema
G
Departamento de Química Orgánica, Universidad de Salamanca, E-37008 Salamanca, Spain. mgrande@usal.es
Grande
Manuel
M
Anaya
Josefa
J
D004852:Epoxy Compounds / Q000737:chemistry; D005609:Free Radicals; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D009942:Organometallic Compounds; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis*
D004852:Epoxy Compounds; D005609:Free Radicals; D006575:Heterocyclic Compounds, 3-Ring; D009942:Organometallic Compounds; D047090:beta-Lactams; C020528:titanocene dichloride