Asymmetric Synthesis of Bicyclo[1.1.0]butyl, Azabicyclo[1.1.0]butyl, and Bicyclo[1.1.1]pentyl Sulfoximines using a SuFEx Reaction

A sulfoxide-metal exchange reaction provides organometallic bicyclo[1.1.0]butyl, 1-azabicyclo[1.1.0]butyl, and bicyclo [1.1.1]pentyl reagents from the corresponding sulfoxides. Subsequent in situ SuFEx reactions with highly enantioenriched sulfonimidoyl fluoride precursors derived from (S)-N-(diisopropylcarbamoyl)-2-methylpropane-2-sulfonimidoyl fluoride (t-BuSF) allow for the asymmetric synthesis of novel bicyclo[1.1.0]butyl, 1-azabicyclo[1.1.0]butyl, and bicyclo[1.1.1]pentyl sulfoximines. These novel building blocks can be used for strain-release transformations and applications in medicinal chemistry.