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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
An approach for rapid increase in molecular complexity: atom economic routes to fused polycyclic ring systems
Barry M Trost1, Veronika Ehmke
1Department of Chemistry, Stanford University , Stanford, California 94305-5080, United States.
Abstract:
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.
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