Enantioselective β-Selective Addition of Isoxazolidin-5-ones to Allenoates Catalyzed by Quaternary Ammonium Salts

The enantioselective addition of isoxazolidin-5-ones to the.-carbon of allenoates has been carried out by using a novel spirobiindane-based quaternary ammonium salt catalyst. This protocol, which proceeds under classical liquid-solid phase-transfer conditions, gives access to unprecedented highly functionalized beta(2,2)-amino acid derivatives with good enantioselectivities and in high yields, and further manipulations of these products have been carried out as well.

Automated summary

The enantioselective addition of isoxazolidin-5-ones to the α-carbon of allenoates has been achieved using a novel spirobiindane-based quaternary ammonium salt catalyst under classical liquid-solid phase-transfer conditions. This method provides unprecedented highly functionalized β(2,2)-amino acid derivatives with good enantioselectivities and high yields. Further manipulations of the products have also been conducted.