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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Addition of electrophilic and heterocyclic carbon-centered radicals to glyoxylic oxime ethers
Stephen B McNabb1, Masafumi Ueda, Takeaki Naito
1Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
Abstract:
[reaction: see text] Stabilized primary radicals can be formed from alkyl halides in an atom transfer process with Et(3)B. This process depends on the strength of the carbon-halogen bond and the stability of the resulting primary radical. Radicals formed from benzyl iodide and ethyl iodoacetate add to glyoxylic oxime ethers; however, more electrophilic radicals do not. Glyoxylic oxime ethers are also good radical acceptors for heterocyclic carbon-centered secondary radicals, giving novel alpha-amino acid derivatives.
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