Enantioselective synthesis of 1,3-bicyclo[2.1.1]hexanes as meta -benzene bioisosteres (opens in new tab)

Bicyclo[2.1.1]hexanes are rigid bridged scaffolds with well-defined exit vectors that have been proposed as appropriate bioisosteres of phenyl rings. Although many racemic syntheses have recently emerged, access to single enantiomers of these skeletons remains a major challenge. Here we have developed an enantioselective copper-catalysed protoborylation to obtain 1,3-disubstituted bicyclo[2.1.1]hexanes as suitable mimics of meta-benzenes. The stereocontrolled formation of these bicyclic frame...