Configurationally stable ε-amido-propargylindiums,
generated in situ from N-Ts-4-ethynylazetidin-2-ones
in the presence of InI, catalytic amounts of Pd(PPh3)4, and N-methylimidazole or pyridine ligand
react with unusual regioselectivity with aromatic and aliphatic aldehydes
to afford 2,6-syn- or 2,6-anti-allenediols
with excellent central-to-axial chirality transfer and useful levels
of acyclic remote 1,5-stereocontrol.
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