Silver catalysed asymmetric [3+2] cycloaddition for the construction of 5−5-membered 1,3'-indolyl pyrrole atropisomers

Abstract

An atropoenantioselective Ag-catalysed [3+2] cycloaddition of N-alkynyl ketones with isocyanides has been developed to access 5−5-membered 1,3'-indolyl pyrroles bearing C-N axial chirality in high yields and excellent enantioselectivities. The resulting products exhibit excellent thermal stability and, upon derivatisation to monophosphine compounds, serve as effective chiral ligands in Pd-catalysed asymmetric reactions.