Anti-Diastereo- and Enantioselective Carbonyl (Hydroxymethyl)allylation from the Alcohol or Aldehyde Oxidation Level: Allyl Carbonates as Allylmetal Surrogates

摘要

The hydroxymethyl 1,3-diol motif appears in numerous natural products, yet asymmetric methods for carbonyl (hydroxymethyl)-allylation are largely unexplored. In most cases, catalytic carbonyl hydroxymethylation has been accomplished through umpolung of palladium π-allyl complexes derived from 2-butene-1,4-diol carboxy-lates or vinyl epoxides in combination with metallic reductants, such as SnCl_2 or InI.