Neutral Chiral Tetrakis-Iodo-Triazole Halogen-Bond Donor for Chiral Recognition and Enantioselective Catalysis.

Chemistry : a European Journal
Florian OstlerOlga García Mancheño

Abstract

Halogen bonding represents a powerful tool in the field of noncovalent interactions. However, applications in enantioselective recognition and catalysis remain almost nonexistent, due in part to the distinct features of halogen bonds, including long covalent and noncovalent bond distances and high directionality. Herein, this work presents a novel chiral tetrakis-iodo-triazole structure as a neutral halogen bond donor for both chiral anion-recognition and enantioinduction in ion-pair organocatalysis. NMR-titration studies revealed significant differences in anion affinity between the halogen bonding receptor and its hydrogen bonding parent. Selective recognition of chiral dicarboxylates and asymmetric induction in a benchmark organocatalytic reaction were demonstrated using the halogen bond donor. Inversions in the absolute sense of chiral recognition, enantioselectivity, and chiroptical properties relative to the related hydrogen donor were observed. Computational modeling suggested that these effects were the result of distinct anion-binding modes for the halogen- versus hydrogen-bond donors.

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Citations

Jun 4, 2021·The Journal of Physical Chemistry. a·Jordan Lapp, Steve Scheiner
Jun 20, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Raphaël RobidasStefan M Huber
Jul 29, 2021·Inorganic Chemistry·Chunyang LiAlexandre Martinez
Jul 27, 2021·The Journal of Physical Chemistry. a·Steve Scheiner
Jun 24, 2021·Chemistry : a European Journal·Andreas BoelkeBoris J Nachtsheim

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Methods Mentioned

BETA
circular dichroism

Software Mentioned

Gaussian16

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