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  • Title: Tandem carbon-carbon bond-forming radical addition-cyclization reaction of oxime ether and hydrazone.
    Author: Miyabe H, Ueda M, Fujii K, Nishimura A, Naito T.
    Journal: J Org Chem; 2003 Jul 11; 68(14):5618-26. PubMed ID: 12839454.
    Abstract:
    The novel tandem radical addition-cyclization of oxime ethers and hydrazones intramolecularly connected with the alpha,beta-unsaturated carbonyl group is described. The radical reaction of oxime ethers 1, 2, and 4 connected with acryloyl and methacryloyl moieties proceeded smoothly to give the heterocycles via a tandem C-C bond-forming process. The tandem reaction of hydrazone 5 took place in the presence of Zn(OTf)(2) as a Lewis acid to give the trans-cyclic product 17 without the formation of the cis-isomer. The diastereoselective radical addition-cyclization reaction of chiral oxime ether 19 was also studied. The tandem reaction of 19 proceeded smoothly even in aqueous media, providing the novel method for asymmetric synthesis of gamma-butyrolactones and beta-amino acid derivatives.
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