Stereoselective synthesis of trans β-lactams via palladium/N-heterocyclic carbene-catalyzed carbonylative [2+2] cycloaddition |
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Authors: | Pan Xie Bo Qian Hanmin Huang Chungu Xia |
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Institution: | State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China |
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Abstract: | The carbonylative 2+2] cycloaddition of benzyl chlorides and allyl derivatives with imines and CO for synthesis of β-lactam is effectively catalyzed by palladium/N-heterocyclic carbene complex. The desired β-lactam could be obtained in good to excellent yields (61–96%) with excellent regioselectivities (trans/cis > 95:5) and chiral lactams could be obtained with moderate diastereoselectivities. The KIE experimental studies have revealed that the C–H cleavage is most likely to be the rate-limiting step for the carbonylative cycloaddition. |
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