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Paper | Special issue | Vol 101, No. 2, 2020, pp.486-495
Published online, 13th August, 2019
DOI: 10.3987/COM-19-S(F)31
Oxidative C-C Bond Cleavage of N-Protected Cyclic Amines by HNO3-TFA System

Kosuke Yamamoto, Hiroyuki Toguchi, Toshihiro Harada, Masami Kuriyama, and Osamu Onomura*

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Oxidative C-C bond cleavage of N-protected cyclic amines was achieved by using 70% HNO3 in trifluoroacetic acid (TFA) to afford ω-amino acid derivatives in high yields. The C-C bond cleavage reaction smoothly proceeded under aerobic condition with a simple procedure. The use of 70% HNO3 as an oxidant source enabled to conduct the reaction at a higher substrate concentration than that of the previous condition using NaNO2 in TFA. In addition, some ω-amino acids were obtained with improved reaction efficiency under the present reaction conditions.