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Communication | Special issue | Vol 88, No. 2, 2014, pp.919-927
Published online, 6th September, 2013
DOI: 10.3987/COM-13-S(S)81
A Catalytic C-C Bond-Formation with Minimal Use of Protecting Groups: Construction of Functionalized Isotetronic Acid Derivatives

Yohei Shimizu,* Kouji Yasuda, and Motomu Kanai*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

A catalytic method to construct multi-functionalized isotetronic acids was developed using cyclic hemiacetals and pyruvic acid derivatives as substrates. The key to success was the combination of catalytic amounts of iron(III) trifluoroacetate and 2-mercaptopyridine. A catalytic asymmetric variant was also developed using 6,6’-dimethoxy-binaphthyl phosphate instead of 2-mercaptopyridine.