Related Experiment Video
Updated: May 8, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
Published on: March 25, 2017
The acylative kinetic resolution of 1,2-azaborine naphthols
Martha I Prindl1, Aidan P McKay1, David B Cordes1
1EaStCHEM, School of Chemistry, University of St Andrews St Andrews KY16 9ST Fife UK ads10@st-andrews.ac.uk.
Abstract:
The enantioselective synthesis of atropisomeric molecules containing stereogenic axes is becoming increasingly important due to their growing incorporation within medicinally relevant compounds. Organocatalytic routes to selectively prepare highly enantioenriched stereogenic axes containing a carbon(sp2)-boron(sp2) bond remain underdeveloped due to the inherent challenge of the longer C-B bond length (1.58 Å) compared to its C(sp2)-C(sp2) counterpart (1.49 Å). This manuscript showcases the development of an isothiourea catalysed acylative kinetic resolution of 1,2-azaborine frameworks to prepare configurationally stable carbon-boron stereogenic axes with good to excellent stereocontrol (24 examples, selectivity factors up to >200). The scope and limitations of this process have been investigated, with product derivatisation and racemisation studies providing insight into the configurational stability of these species and the association between boron hybridisation and atropisomeric stability. Building on insight gained from these studies preliminary proof of principle investigations concerning an acylative dynamic kinetic resolution in this system has been demonstrated.
More Related Videos
Related Concept Videos
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Nucleophilic Aromatic Substitution: Elimination–Addition
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

