Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide-alkyne cycloadditions

Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide-alkyne cycloaddition

Asymmetric copper catalyzed azide-alkyne cycloadditions

Since its discovery independently by Sharpless and Meldal in 2002, the copper-catalyzed azide–alkyne cycloaddition (CuAAC) has become a ubiquitous molecular linking platform. Easy access to substituted 1,4-triazoles can be exploited to engender asymmetry to a myriad of potentially useful targets in high yields. Utilizing the CuAAC to form chiral triazolic products in a single step is an attractive and powerful approach for the synthetic chemist. The area of asymmetric CuAAC is still in its infancy compared to more established asymmetric metal-mediated transformations; however, this leads to exciting challenges that need to be overcome to usher in the next era in the story of the triazole and click chemistry in general. This review details the steps taken into asymmetric CuAAC and the exciting results achieved thus far. [Note that diagrams accompany this abstract in the published version and can be found at http://dx.doi.org/10.1021/acscatal.6b00996.

Glucose selective bis-boronic acid click-fluor

Four novel bis-boronic acid compounds were synthesised via copper catalysed azide–alkyne cycloaddition (CuAAC) reactions.</p

Synthesis of atropisomeric phosphino-triazoles and their corresponding gold(i) complexes

The synthesis of atropisomeric phoshino-triazoles is disclosed. It was found that the introduction of a phosphine functionality onto the 5-position of a 1,2,3-triazole ring could be highly restrictive towards the rotation around a triazole-aryl bond. VT NMR and chiral HPLC studies demonstrated that rotation was restricted even at high temperatures. Gold(I) chloride complexes of single-enantiomer phosphines were prepared and again demonstrated to be conformationally stable

γ-Lactams and furan bispyrrolidines via iodine mediated cyclisation of homoallylamines

1,3,5-Substituted pyrrolidin-2-ones were synthesisedviaan iodine mediated cyclisation of 3-methyl substituted homoallylamines in good to excellent yield, as mixtures of diastereoisomers. Furan bispyrrolidines were formed as single diastereoisomers when 3-phenyl homoallylamines were employed in an analogous reaction.</p

Selective glycoprotein detection through covalent templating and allosteric click-imprinting

A hierarchical bottom-up route exploiting reversible covalent interactions with boronic acids and so-called click chemistry for selective glycoprotein detection is described. The self-assembled and imprinted surfaces confer high binding affinities, nanomolar sensitivity, exceptional glycoprotein specificity and selectivity.</p