Chemoselective cyclization of N-sulfonyl ketimines with ethenesulfonyl fluorides: Access to trans -cyclopropanes and fused-dihydropyrroles

Abstract

An interesting stereo- and chemoselective cyclization reaction of several N-sulfonyl ketimines as C/N-donors with a variety of α,β-unsaturated sulfonyl fluorides promoted by DBU is reported. This substrate-dependent selective C-C vs. C-N bond cyclization process leads to important classes of trans-cyclopropane and fused dihydropyrrole scaffolds in satisfactory yields with excellent diastereoselectivities (dr up to ≤99:1). High-yield single-stage synthesis of biologically interesting sulfamate-fused-pyrrole and 2-pyrrolyl phenol derivatives was successfully established. © 2019 The Royal Society of Chemistry.