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

DOI Web Site Web Site 被引用文献1件 参考文献81件

書誌事項

タイトル別名
  • Integrated Reactions Using Addition to Conjugated Imines and Iminium Salts
  • キョウヤク イミン オヨビ イミニウムエン エ ノ フカ ハンノウ オ キジク ト スル ハンノウ ノ シュウセキカ

この論文をさがす

抄録

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.

収録刊行物

被引用文献 (1)*注記

もっと見る

参考文献 (81)*注記

もっと見る

関連プロジェクト

もっと見る

キーワード

詳細情報 詳細情報について

問題の指摘

ページトップへ