Non-biaryl atropisomerism at the C–B bond in sterically hindered aminoarylboranes
Mélodie Birepinte, Frédéric Robert, Sandra Pinet, Laurent Chabaud, Mathieu Pucheault
Abstract
Sterically hindered aminoarylboranes featuring atropisomerism about the C-B bond were prepared by addition of organomagnesium species onto readily accessible dialkylamine-borane complexes. Some of these aminoarylboranes, isosteres of vinyl styrene derivatives, were resolved by HPLC on the chiral stationary phase. They are the first examples of a non-biaryl type system which display slow rotation about a C-B bond.
Topics & Concepts
AtropisomerSteric effectsChemistryStereochemistryBondBusinessFinanceAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis