2009Chemical CommunicationsRequires access

Conjugated imines and iminium salts as versatile acceptors of nucleophiles

Makoto Shimizu, Iwao Hachiya, Isao Mizota

Open publisher page 106 citations

Abstract

Growing interests in nitrogen-containing molecules involving bioactive and functional materials have stimulated the recent development of synthetic methodologies where nucleophilic addition reactions to imino carbons are utilized in crucial steps. This article summarizes double nucleophilic addition reactions with alpha,beta-unsaturated aldimines, addition reactions using alkynyl imines, "umpoled" reactions of alpha-imino esters, and the use of iminium salts as reactive electrophiles.

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What this paper is about

Growing interests in nitrogen-containing molecules involving bioactive and functional materials have stimulated the recent development of synthetic methodologies where nucleophilic addition reactions to imino carbons are utilized in crucial steps. This article summarizes double nucleophilic addition reactions with alpha,beta-unsaturated aldimines, addition reactions using alkynyl imines, "umpoled" reactions of alpha-imino esters, and the use of iminium salts as reactive electrophiles.

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OpenAlex reports 106 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

Growing interests in nitrogen-containing molecules involving bioactive and functional materials have stimulated the recent development of synthetic methodologies where nucleophilic addition reactions to imino carbons are utilized in crucial steps. This article summarizes double nucleophilic addition reactions with alpha,beta-unsaturated aldimines, addition reactions using alkynyl imines, "umpoled" reactions of alpha-imino esters, and the use of iminium salts as reactive electrophiles.

Key concepts: Iminium, Nucleophile, Conjugated system, Chemistry, Combinatorial chemistry, Organic chemistry, Ion, Catalysis

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