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Highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl esters via Sc(OTf)3-catalyzed imino mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines

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JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 13, 页码 5016-5019

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AMER CHEMICAL SOC
DOI: 10.1021/jo070533r

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Functionalized gamma-lactams are found to be crucial intermediates in the synthesis of biologically important natural products. We herein described a highly diastereoselective synthesis of beta-carboxy-gamma-lactams and their ethyl ester derivatives, in high yields with high diastereomeric ratio, via the Mukaiyama-aldol type reaction of 2,5-bis(trimethysilyloxy)furan with imines, employing Sc(OTf)(3) as a catalyst.

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