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Paper | Regular issue | Vol 89, No. 1, 2014, pp.143-169
Published online, 13th December, 2013
DOI: 10.3987/COM-13-12881
Preparation of Cyclic β-Amino Acid Derivatives with Quaternary Carbon Center via a Radical Addition-Cyclization Sequence

Norihiko Takeda, Masafumi Ueda, Seiko Kajisa, Kenji Matsuno, Takeaki Naito, and Okiko Miyata*

*Department of Medicinal Chemistry, Kobe Pharmaceutical University, 4-19-1, Motoyamakitamachi, Higashinada, Kobe 658-8558, Japan

Abstract

A new method has been developed for the construction of α,α-disubstituted cyclic β-amino acid derivatives via the sulfanyl radical addition-cyclization reaction of oxime ether connected with acrylate. This reaction proceeded smoothly to give the cyclized products that contained a quaternary carbon center. Furthermore, the use of carbon centered radicals in the reaction allowed for the formation of cyclic amines containing various alkyl chains. The cyclized product with a quaternary carbon center could also be converted to sterically congested cyclic β-amino acid.