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The Direct Synthesis of Unsymmetrical Vicinal Diamines from Terminal Alkynes: A Tandem Sequential Approach for the Synthesis of Imidazolidinones

TitleThe Direct Synthesis of Unsymmetrical Vicinal Diamines from Terminal Alkynes: A Tandem Sequential Approach for the Synthesis of Imidazolidinones
Publication TypeJournal Article
Year of Publication2009
AuthorsLee, AV, Sajitz, M, Schafer, LL
JournalSynthesis-Stuttgart
Pagination97-104
Date PublishedJan
Type of ArticleArticle
ISBN Number0039-7881
KeywordsAMINES, ANTI-MARKOVNIKOV, ASYMMETRIC-SYNTHESIS, CATALYZED INTERMOLECULAR HYDROAMINATION, HETEROCYCLES, HYDROAMINATION, IMIDO COMPLEXES, INTRAMOLECULAR HYDROAMINATION, LIGANDS, SCOPE, tandem reactions, TITANIUM, TITANIUM PRECATALYST, VINYLARENES
Abstract

The combination of titanium-catalyzed anti-Markovnikov hydroamination of terminal alkynes with the Strecker reaction is used in the synthesis of unsymmetrical vicinal diamines via the one-pot synthesis of alpha-cyanoamines. This methodology is Further applied to the efficient synthesis of imidazolidinones. An easy-to-use bis(amidate)titanium precatalyst permits efficient approaches to heterocyclic chemistry from terminal alkynes.
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