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Paper | Special issue | Vol 79, No. 1, 2009, pp.739-751
Published online, 10th December, 2008
DOI: 10.3987/COM-08-S(D)39
Intermolecular Carbon Radical Addition to Cyclic Nitrone

Masafumi Ueda, Hideto Miyabe, Nami Nonoguchi, Okiko Miyata, Osamu Tamura, and Takeaki Naito*

*Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan

Abstract

The intermolecular radical addition to chiral glyoxylic nitrone was studied. The ethyl radical addition to nitrone by using triethylborane proceeded smoothly to give the desired ethylated product with moderate diastereoselectivities accompanying with the ethylated nitrone and the diethylated product. The radical reaction of nitrone took place even in aqueous media. The investigation of optimal reaction conditions and the reaction pathway were described.