ol5009872_si_002.cif (42.44 kB)

An Approach for Rapid Increase in Molecular Complexity: Atom Economic Routes to Fused Polycyclic Ring Systems

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posted on 16.05.2014, 00:00 by Barry M. Trost, Veronika Ehmke
A protocol for the asymmetric trimethylenemethane (TMM) [3 + 2] cycloaddition reaction of alkynyl-substituted TMM donors and unsaturated N-acyl pyrroles employing a chiral bisdiamidophosphite ligand has been developed. This process generates alkynyl-substituted cyclopentanes in high yields and diastereo- and enantioselectivities. These chiral precursors are employed for the atom economic assembly of fused polycyclic hydrocarbons with hydroindene, hydroazulene, and hydro­cyclo­penta­naph­thalene scaffolds by consecutive cycloaddition reactions.