Carbon Radical Addition to Glyoxylic Oxime Ether via Iodine Atom-Transfer Process

Hideto Miyabe; Masafumi Ueda; Naoko Yoshioka; Takeaki Naito

doi:10.1055/s-1999-2649

Synlett 1999; 1999(4): 465-467
DOI: 10.1055/s-1999-2649

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Carbon Radical Addition to Glyoxylic Oxime Ether via Iodine Atom-Transfer Process

Hideto Miyabe^* , Masafumi Ueda, Naoko Yoshioka, Takeaki Naito

^*Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan; Fax 07 84 41 75 56; E-mail: taknaito@kobepharma-u.ac.jp

Abstract

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Intermolecular carbon radical addition to glyoxylic oxime ether was effectively improved by using alkyl iodides and triethylborane which acts multiply as a Lewis acid, a radical initiator and a terminator. The addition of secondary and tertiary alkyl radicals has provided a new efficient carbon-carbon bond-forming method for the one-pot synthesis of a variety of α-amino acids.

radical addition - oxime ether - atom-transfer - one-pot - α-amino acid

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