1272565-10-2Relevant articles and documents
Divergent reaction pathways of a cationic intermediate: Rearrangement and cyclization of 2-substituted furyl and benzofuryl enones catalyzed by iridium(III)
Vaidya, Tulaza,Manbeck, Gerald F.,Chen, Sylvia,Frontier, Alison J.,Eisenberg, Richard
supporting information; experimental part, p. 3300 - 3303 (2011/05/04)
In contrast to 2-substituted pyrrole enones, furyl and benzofuryl enones do not undergo the Nazarov electrocyclization. Instead, these furyl and benzofuryl enones exhibit unusual rearrangement sequences in the presence of catalytic amounts of [IrBr(CO)(DIM)((R)-(+)-BINAP)](SbF6)2 (1; DIM = diethylisopropylidene malonate) and AgSbF6 (1:1). A 1,2-H shift followed by intramolecular Friedel-Crafts alkylation leads to synthetically valuable cyclohexanones with furanylic quaternary centers. The electrophilicity of 1 is essential for this rearrangement.