Synthesis of Primitive Dendrimer Systems Bearing Bicyclo[3,2,0]Hept-6-en-6-yl Groups via Unique Au-catalyzed [2+2] Cyclization

Abstract

Propargylic pivaloates bearing an alkynyl group at a three-carbon tether under the gold catalysis would undergo [3,3] rearrangements of propargylic pivaloates followed by tandem [2+2] cyclization to give the corresponding 6-acylbicyclo[3,2,0]hept-6-ens. In continuing work, we prepared various substrates bearing two arms of alkyne-propargylic pivaloates to explore primitive dendrimer concept bicyclic compounds. Finally, we could obtain a series of diasteromeric compounds bearing two arms of 6-acylbicyclo[3,2,0]hept-6-ene groups in high yields.