Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles

Nicholas J. Race, Ian R. Hazelden, Adele Faulkner, John F. Bower

Research output: Contribution to journalReview article

47 Scopus citations

Abstract

Aza-Heck cyclizations are an emerging method for the construction of chiral N-heterocyclic systems. In these processes, an activated N-O bond replaces the C-X bond (X = halide, OTf) used in conventional Heck reactions, with the associated aza-Pd(ii)-intermediate engaging pendant alkenes in a Heck-like manner. This perspective article commences with an historical overview of the area, which stems from Narasaka's seminal studies using oxime esters as the initiating motif. The scope and mechanism of associated chiral N-heterocyclic methodologies are then outlined, including cascade processes that enable diverse alkene 1,2-carboaminations. The recent emergence of new N-O donors and the realization of highly enantioselective aza-Heck cyclizations are then discussed. Collectively, these studies suggest that the aza-Heck approach can underpin a broad family of redox-neutral and enantioselective C-N bond forming processes.

Original languageEnglish (US)
Pages (from-to)5248-5260
Number of pages13
JournalChemical Science
Volume8
Issue number8
DOIs
StatePublished - 2017

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