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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

Supporting Info

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 scmpk@mahidol.ac.th; scvrt@mahidol.ac.th

J. Org. Chem., 2007, 72 (13), pp 5016–5019

DOI: 10.1021/jo070533r

Publication Date (Web): May 17, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Functionalized γ-lactams are found to be crucial intermediates in the synthesis of biologically important natural products. We herein described a highly diastereoselective synthesis of β-carboxy-γ-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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Published In Issue June 22, 2007
Received March 15, 2007

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Note

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