Synthesis of new bioorganometallic Ir- and Rh-complexes having β-lactam containing ligands.
The synthesis (and full spectroscopic and crystallographic characterization) of new classes of bioorganometallic Ir- and Rh-complexes having β-lactam containing ligands has been achieved in three steps starting from simple precursors. The procedure for preparing these bioorganometallic compounds uses β-lactams having a phenylpyridyl moiety attached to the C4, N1 or C4 and N1 positions simultaneously, and a directed C-H metal-insertion, in the presence of (MCp*Cl2)2 (M = Ir, Rh). Enantiomerically pure 2-azetidinones can be transformed into diastereomeric (at the metal) mixtures of enantiopure metalla-2-azetidinones. Bimetallic 2-azetidinones are also accessible by this approach. The insertion of electron-poor alkynes into the M-C bond of the bioorganometallic complex occurs regioselectively and in excellent yields. Overall, the sequence imine-β-lactam-metalla-β-lactam is a versatile and efficient full methodology to prepare and functionalize unprecedented, novel Ir- and Rh-complexes having β-lactam containing ligands.
Departamento de Química Orgánica, Facultad de Química, Universidad Complutense, 28040, Madrid, Spain. luis_casarrubios@quim.ucm.es sierraor@ucm.es.
Jaime G
JG
Muntaner
Luis
L
Casarrubios
Miguel A
MA
Sierra
D007495:Iridium / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012211:Rhenium / Q000737:chemistry*
D007769:Lactams; D008024:Ligands; D009942:Organometallic Compounds; D007495:Iridium; D012211:Rhenium