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Issue 8, 2017
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Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles

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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.

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

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Publication details

The article was received on 03 Apr 2017, accepted on 22 May 2017 and first published on 20 Jun 2017


Article type: Perspective
DOI: 10.1039/C7SC01480E
Citation: Chem. Sci., 2017,8, 5248-5260
  • Open access: Creative Commons BY license
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    Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles

    N. J. Race, I. R. Hazelden, A. Faulkner and J. F. Bower, Chem. Sci., 2017, 8, 5248
    DOI: 10.1039/C7SC01480E

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