Metallic base-induced cycloadditions of N-(1-cyanoalkyl)imines via N-metalated azomethine ylides: Enhanced reactivity and high regio- and stereoselectivity.

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概要

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• Lithiation of <I>N</I>-(1-cyanoalkyl)imines with LDA generates new <I>N</I>-lithiated azomethine ylide 1,3-dipoles which show enhanced reactivity toward dipolarophiles. They undergo exclusively regio- and stereoselective 3+2 cycloaddition reaction with α,β-unsaturated esters to give 1-pyrrolines after the elimination of LiCN. Metallic bases other than LDA can be also effective. Such high regio- and stereoselectivity is explained by the involvement of <I>N</I>-metalated azomethine ylides.

• 公益社団法人 日本化学会の論文

著者

• Yorozu Kiyotaka

  Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University

関連論文

• Simple generation of ester-stabilized azomethine ylides from 2-amino esters and carbonyl compounds. Stereochemistry of their cycloadditions.
• 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.
• Metallic base-induced cycloadditions of N-(1-cyanoalkyl)imines via N-metalated azomethine ylides: Enhanced reactivity and high regio- and stereoselectivity.

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