Towards Atropoenantiopure N–C Axially Chiral Compounds via Stereoselective C–N Bond Formation

Authors

  • Johanna Frey Laboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg / Université de haute Alsace, ECPM, 25 Rue Becquerel, 67087 Strasbourg, Franc
  • Sabine Choppin Laboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg / Université de haute Alsace, ECPM, 25 Rue Becquerel, 67087 Strasbourg, Franc
  • Françoise Colobert Laboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg / Université de haute Alsace, ECPM, 25 Rue Becquerel, 67087 Strasbourg, Franc
  • Joanna Wencel-Delord Laboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg / Université de haute Alsace, ECPM, 25 Rue Becquerel, 67087 Strasbourg, Franc

DOI:

https://doi.org/10.2533/chimia.2020.883

PMID:

33243324

Keywords:

Asymmetric synthesis, Axial chirality, Hypervalent iodine, C–n axial chirality, N–c atropisomerism, N–c axial chirality

Abstract

N–C axial chirality, although disregarded for decades, is an interesting type of chirality with appealing applications in medicinal chemistry and agrochemistry. However, atroposelective synthesis of optically pure compounds is extremely challenging and only a limited number of synthetic routes have been designed. In particular, asymmetric N-arylation reactions allowing atroposelective N–C bond forming events remain scarce, although great advances have been achieved recently. In this minireview we summarize the synthetic approaches towards synthesis of N–C axially chiral compounds via stereocontrolled N–C bond forming events. Both organo-catalyzed and metal-catalyzed transformations are described, thus illustrating the diversity and specificity of both strategies.

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Published

2020-11-25