Controlling chirality in the synthesis of 4 + 4 diastereomeric amine macrocycles derived from trans-1,2-diaminocyclopentane and 2,6-diformylpyridine.

A few suitably long dialdehyde and primary diamine building blocks of a predetermined chirality have been designed and synthesized to enable controlled and efficient synthesis of all 6 possible diastereomers...

Ligand Centered Redox Enabled Sustainable Synthesis of Triazines and Pyrimidines Using A Zinc-Stabilized Azo-Anion Radical Catalyst

Herein, we report ligand-centered redox controlled Zn(II)-catalyzed multicomponent approaches for synthesizing pyrimidines and triazines. Taking advantage of the ligand-centered redox events, using a well-defined Zn(II)-catalyst (1a) bearing (E)-2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (L1a) as...

Construction of N-heterocycles via Pd-mediated C–H activation/annulation strategies

N-heterocycles can be found in natural products and drug molecules, which are indispensable components in the area of organic synthesis, medicinal chemistry and material science. The construction of these N-containing...

Rh(III)-catalyzed annulated coupling of sulfoxonium ylides and iodonium ylides: a rapid access to isocoumarins

Direct synthesis of isocoumarin skeletons has been realized through Rh(III)-Catalyzed [3 + 3] annulation of sulfoxonium ylides and iodonium carbenes. The synthetic protocol constructed efficiently with the broad functional group...

Synthesis of 2-hydroxytetrahydrofurans by Wacker-type oxidation of 1,1-disubstituted alkenes

1,1-Disubstituted alkenes feature high steric hindrance, which renders their Wacker-type oxidation difficult. We demonstrated the stereoselective synthesis of 2-hydroxytetrahydrofurans via the Wacker-type oxidation of 3-methyl-3-buten-1-ols by using a PdCl2(MeCN)2/NO/BQ catalyst...

Recent developments in the utility of saturated azaheterocycles in peptidomimetics

To large extent, the physical and chemical properties of peptidomimetic molecules are dictated by the integrated heterocyclic scaffolds they contain. Heterocyclic moieties are introduced into a majority of peptide-mimicking molecules...

Silver Salt Enabled H/D Exchange at β Position of Thiophene Rings: Synthesis of Fully Deuterated Thiophene derivatives

We disclose a silver catalyzed H/D exchange reaction, which can introduce deuterium atom at β position of thiophene rings without the assisstance of any coordinating groups. The advantages of this...

Deuterium Labelling to Extract Local Stereochemical Information by VCD Spectroscopy in C-D Stretching Region: A Case Study of Sugars

Stereochemical elucidation of molecules with multiple chiral centers is difficult. Even with VCD spectroscopy, excluding all but one diastereomeric structural candidates is challenging because stereochemical inversion of one chiral center...

A DFT examination of the role of proximal boron functionalities in the S-alkylation of sulfenic acid anions

DFT modelling predicts proximal boron groups can accelerate sulfenate alkylation reactions, depending on boron substituents and boron distance from the reaction site.