Development of Domino Reactions Based on Radical Addition Reaction to Conjugated Oxime Ethers

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  • 共役オキシムエーテル類へのラジカル付加反応を基盤としたドミノ型反応の開発
  • キョウヤク オキシムエーテルルイ エ ノ ラジカル フカ ハンノウ オ キバン ト シタ ドミノガタ ハンノウ ノ カイハツ

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Abstract

The synthetic utilities of conjugated oxime ethers as a radical acceptor are described. The triethylborane-mediated intermolecular carbon radical addition to chiral conjugated oxime ether proceeded regio- and stereoselectively. The radical reaction of conjugated oxime ether with triethylborane in the presence of aldehyde afforded γ-butyrolactone via sequential process involving ethyl radical addition, generation of N-boryl enamine, aldol-type reaction with aldehyde and lactonization. On the other hand, treatment of conjugated oxime ether with triethylborane and thiophenol in the presence of O2 gave β-hydroxysulfides with high regioselectivity and good yield. The reaction would proceed through radical pathway involving regioselective addition and the subsequent trapping of the resulting α-imino radical with O2, where the imino group enhances the stability of the intermediate radical. The hydroxyalkylation reaction via carbon radical addition and hydroxylation with O2 was also developed.

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