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[2+2] Carbonylative cycloaddition catalyzed by palladium: stereoselective synthesis of β-lactams |
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| Authors: | Luigino Troisi Luisella De Vitis Tullio Pilati |
| Affiliation: | a Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università di Lecce, Via Prov.le Lecce-Monteroni, I-73100 Lecce, Italy b CNR “Institute of Molecular Science and Technology”, University of Milan, Via C. Golgi 19, I-20133 Milan, Italy |
| Abstract: | [2+2] Carbonylative cycloaddition of chiral imines to various allyl halides, under CO pressure, in the presence of Et3N, a catalytic amount of Pd(OAc)2 and PPh3 as ligand, are carried out. Separable diastereomeric mixtures of chiral alkenyl-β-lactams are isolated with good yields and high trans diastereoselections. Absolute configurations are assigned by X-ray measurements and 1H NMR spectroscopy. |
| Keywords: | Chiral β-lactams Enantiopure imines Carbonylative cycloaddition Stereoselectivity |
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