Synthesis of Polyisocyanide Compounds via α-Metalation Reactions

Michael G. Hill, Matthew C. Comstock, Kent R. Mann

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

α-Metalated isocyanides were first prepared over 20 years ago1and have since become useful reagents in organic synthesis,2a-cBecause the isocyanide group is readily hydrolyzed to the corresponding amine, metalated iso-cyanides provide a convenient means of nucleophilic introduction of α-aminoalkyl groups into organic molecules. For example, the reaction of metalated 2-isocyanopropionic ester with benzylbromide provides, following acid hydrolysis, α-methylphenylalanine.3Alternatively, reactions of α-Metalated isocyanides with various electrophilic reagents such as ketones, thioketones, Schiff bases, etc., permit an efficient route to the resulting heterocycles (oxazolines, thiazolines, imidazolines, etc.).

Original languageEnglish (US)
Pages (from-to)4950-4951
Number of pages2
JournalJournal of Organic Chemistry
Volume55
Issue number16
DOIs
StatePublished - Jan 1 1990

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