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

Manat Pohmakotr,* Nattawut Yotapan, Patoomratana Tuchinda, Chutima Kuhakarn and Vichai Reutrakul*

*Department of Chemistry, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand, Email: scmpkmahidol.ac.th, scvrtmahidol.ac.th

M. Pohmakotr, N. Yotapan, P. Tuchinda, C. Kuhakarn, V. Reutrakul, J. Org. Chem., 2007, 72, 5016-5019.

DOI: 10.1021/jo070533r

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Abstract

A highly diastereoselective reaction of 2,5-bis(trimethysilyloxy)furan with imines gives β-carboxy-γ-lactams and their ethyl ester derivatives in high yields via a Mukaiyama-aldol type reaction with high diastereomeric ratio employing Sc(OTf)₃ as catalyst.

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Key Words

γ-lactams

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ID: J42-Y2007-2070