Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

Abstract

The synthesis and characterisation of axially chiral atropisomeric 1,5-disubstituted 1,2,3-triazoles is reported. Molecules designed to display restricted rotation about 1,2,3-triazole N-1-aryl or 1,2,3-triazole C-5-aryl bonds were investigated by physical and computational techniques. The barrier to 1,2,3-triazole N-1-aryl rotation was found to be higher than that for 1,2,3-triazole C-5-aryl rotation, confirming axial chirality stemming from restricted rotation about an N-1-aryl bond in a 1,5-disubstituted 1,2,3-triazole to be the most suitable for the development of an axial chirality triazole-based platform.

Tetrahedron looking back, Tetrahedron Chem looking forward

“…We also have nine research articles. The axial chirality thread continues in a study by John Fossey and co-workers on the restricted rotation of axially chiral atropisomeric 1,5-disubstituted triazole systems [5], and C-H activation is exploited by Georg Manolikakes and colleagues, who report a C-H-functionalization and synthesis of sulfonylated N-heterocycles in an operationally simple one-pot procedure [6]. Hiroki Oguri reports his team's successful efforts towards chemo-enzymatic total synthesis of bis-tetrahydroisoquinoline alkaloids [7], and Tim Newhouse and co-workers disclose a concise synthesis of (À)-melazolide B and (À)-actinidiolide [8].…”