An approach for rapid increase in molecular complexity: atom economic routes to fused polycyclic ring systems.
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.
Department of Chemistry, Stanford University , Stanford, California 94305-5080, United States.
Barry M
BM
Trost
Veronika
V
Ehmke
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D003517:Cyclopentanes; D008024:Ligands; D011083:Polycyclic Compounds; D011758:Pyrroles; C522820:trimethylenemethane; D010165:Palladium; D008697:Methane