Asymmetric Three-Component Reaction of Enynal with Alcohol and Imine as An Expeditious Track to Afford Chiral α‑Furyl-β-amino Carboxylate Derivatives

Herein, we report an achiral dirhodium complex and chiral
phosphoric
acid cooperatively catalyzed asymmetric three-component reaction of
enynal with alcohol and imine, affording chiral α-furyl-β-amino
carboxylates in good to high yields with generally excellent stereoselectivity.
The successful introduction of enynal as a carbene precursor in this
reaction provides an expeditious track to prepare complex furan derivatives
with adjacent quaternary and tertiary stereocenters. The starting
materials are stable and readily available, and the method features
100% atom economy with high bond-formation efficiency. This is a highly
enantioselective gem-difunctionalization reaction
of metal carbene generated in situ from enynal. These generated chiral
products could be smoothly converted to polycyclic frameworks and
drug-conjugated derivatives through different cycloaddition reactions.