Michael addition and alkylation of 2-azaallyl anions derived from N-(1-cyanoalkyl)imines, and stereoselective cyclization of imine esters or ketones leading to 1-pyrrolines.
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概要
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The 2-azaallyl anions derived from <I>N</I>-(1-cyanoalkyl)imines and DBU undergo Michael addition or alkylation to produce <I>N</I>-(1-alkylated 1-cyanoalkyl)imines. The Michael addition of some aryl-substituted imines are highly diastereoselective. The alkylated Michael adducts are converted into lactams through a hydrolysis and recyclization sequence. Base-induced cyclization furnishes 1-pyrrolines through a cyclization and HCN elimination sequence. In the latter reaction, 4,5-<I>cis</I>-1-pyrrolines are selectively produced when the adducts are treated with LDA in the presence of lithium iodide.
- 公益社団法人 日本化学会の論文
著者
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Ueno Kazunori
Institute For Materials Research Tohoku University
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Kanemasa Shuji
Institute Of Advanced Material Study Kyushu University
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Yorozu Kiyotaka
Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
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Tsuge Otohiko
Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
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Tsuge Otohiko
Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences
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