Oxahelicene NHC ligands in the asymmetric synthesis of nonracemic helicenes

Abstract

A straightforward approach to enantiopure 2H-pyran-modified amino[5]helicenes and amino[6]helicenes was developed. They were converted to 1,3-disubstituted imidazolium salts and used as NHC ligand precursors in the Ni⁰-catalysed enantioselective [2+2+2] cycloisomerisation of aromatic triynes to obtain the model helicene derivatives in up to 86% ee.