Synthesis of New Axially Chiral Iodoarenes

Mathieu Bekkaye; Géraldine Masson

doi:10.1055/s-0035-1560512

Synthesis, Table of Contents

Synthesis 2016; 48(02): 302-312
DOI: 10.1055/s-0035-1560512

paper

Synthesis of New Axially Chiral Iodoarenes

Authors

Mathieu Bekkaye

Institut de Chimie des Substances Naturelles CNRS, Univ. Paris-Sud, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France Email: geraldine.masson@cnrs.fr
Géraldine Masson*

Institut de Chimie des Substances Naturelles CNRS, Univ. Paris-Sud, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France Email: geraldine.masson@cnrs.fr

Abstract

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Abstract

A new family of axially chiral iodoarenes derived from commercially available (R)-1,1′-binaphthyl-2,2′-diamine have been synthesized and employed as catalysts in Kita’s enantioselective oxidative spirolactonization of propanoic acid tethered 1-naphthol. Through this study, we explored the relationship between the hypervalent iodoarene geometry and enantioselectivity, contributing to the current understanding of axial-to-central chirality transfer in organoiodine(III) catalysis.

Key words

chiral iodane - hypervalent iodine - dearomatization - stereoselective synthesis - spirolactonization

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References

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