A 5C + 5C Bicycloaromatization Reaction via an Aldol Condensation Cascade: A Regioselective Synthesis of Functionalized Naphthalenes from Acyclic Precursors

Article abstract of DOI:10.1021/jo00256a002

A regioselective synthesis of naphthalene derivatives 51 was developed by the reaction of 1,3,5-tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene (2) with the 1,3,5-tris-electrophiles 50 and trimethylsilyl triflate.Three carbon-carbon bonds are formed in this aldol condensation cascade, where the regiochemistry is controlled by the different reactivities at the sites of the acyclic precursors.