Chiral Molecular Propellers of Triarylborane Ammonia Adducts.

Angewandte Chemie
Michael KemperChristian Merten

Abstract

Chiral molecular propeller conformations have been induced to various triaryl structures including trityl derivatives and triaryl boranes. For borane-amine adducts, such induced propeller chirality has not been reported yet due to the low energy barrier for racemization in common triarylboranes such as B(C6 H5 )3 or B(C6 F5 )3 . Herein, we demonstrate that point chirality in side chains of chiral triarylborane-ammonia adducts, which feature intramolecular hydrogen bonds in addition to the dative N→B bond, can efficiently be transferred to triarylborane propeller chirality. Employing X-ray crystallography and ECD/VCD spectroscopy for structural characterizations, we investigate three examples with different steric demands of the incorporated chiral alkoxy side groups. We elucidate the conformational preferences of the molecular propellers. Furthermore, we show that computationally predicted conformational preferences obtained for the isolated, only implicitly solvated molecules are actually opposite to the experimentally observed ones.

References

Nov 9, 2002·Organic Letters·Chambers C HughesDirk Trauner
Aug 19, 2009·Angewandte Chemie·Jacek ScieburaJacek Gawronski
Jun 23, 2011·Angewandte Chemie·Hiroshi ItoKazuhiko Saigo
Jul 10, 2013·The Journal of Organic Chemistry·Gennaro PescitelliFabrizio Santoro
Feb 12, 2014·Physical Chemistry Chemical Physics : PCCP·Christian MertenWolfram Sander
Jun 3, 2016·The Journal of Physical Chemistry. a·Tobias OsowskiChristian Merten
Aug 9, 2016·The Journal of Organic Chemistry·Li WangSheryl L Wiskur
Jun 1, 2017·Physical Chemistry Chemical Physics : PCCP·Christian Merten
May 3, 2019·The Journal of Organic Chemistry·Christian MertenNora M Kreienborg
Aug 7, 2020·Physical Chemistry Chemical Physics : PCCP·Jonathan BogaertsChristian Johannessen

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Citations

Jun 24, 2021·The Journal of Organic Chemistry·Michał MichalakMarcin Górecki
Nov 4, 2021·Physical Chemistry Chemical Physics : PCCP·Tino P Golub, Christian Merten

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Methods Mentioned

BETA
NMR
X‐ray
circular dichroism

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