共役イミンおよびイミニウム塩への付加反応を基軸とする反応の集積化

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概要

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• An intriguing umpolung of the reactivity of imines possessing electron-withdrawing groups was observed. For example, N-alkylation/coupling reaction of the imines derived from glyoxylates was conducted with dialkylaluminum chloride in acetonitrile to give N-monoalkylated 1,2-diamines in good yields. On treatment of various α-imino esters with organoaluminum reagents and allyltributhyltin in the presence of benzoyl peroxide (BPO), the tandem reaction proceeded to give the N-alkylation/C-allylation products in good yields. Diethyl 2-[N-(p-methoxyphenyl)imino]malonate underwent amination reactions with alkyl Grignard reagents to give N-alkylation products in good yields. The obtained N-alkylation products were readily converted into N-alkyl-p-anisidines by the oxidative removal of the malonate moiety. In order to enhance the reactivity of imines, an iminium salt was prepared using the oxidation of amino ketene silyl acetal with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), and the subsequent nucleophilic addition to this iminium species proceeded to afford α-amino esters in good yields.

• 2011-10-01

著者

• 清水 真

  三重大学大学院工学研究科分子素材工学専攻

• 波多 慎吾

  三重大学大学院工学研究科分子素材工学専攻

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• 共役イミンおよびイミニウム塩への付加反応を基軸とする反応の集積化

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