Synthesis of homochiral 3-substituted cyclopentanones from 2-norbornanones

Article abstract of DOI:10.1016/0957-4166(96)00264-9

The cleavage of the C₁-C₂ bond in norbornate derivatives is accomplished by base-promoted hydrolysis of α-nitroketones, periodate oxidation or Beckmann fragmentation of suitable precursors prepared from the 2-norbornanones 1. These reactions are the basis for the synthesis of the 3-substituted homochiral cyclopentanones 6, 10 or 15.