Diastereo- and Enantioselective Synthesis of 2,2-Disubstituted Benzofuran-3-one Bearing Adjacent Quaternary and Tertiary Stereocenters

The
first highly diastereo- and enantioselective synthesis of armeniaspirol
analogues was achieved using L-proline derived bifunctional
squaramide which outperformed commonly used organocatalysts. Excellent
yield (up to 99%) with diastereoselectivity (up to 99:1) and enantioselectivity
(up to 99%) were obtained for a wide range of substrates.

本研究首次成功实现Armeniaspirol类似物的高非对映选择性与高对映选择性合成，所使用的L-脯氨酸衍生双功能方酰胺（bifunctional squaramide）催化性能优于常规有机小分子催化剂（organocatalysts）。针对宽泛范围的底物，该反应均可取得优异的收率（最高达99%），并实现最高99:1的非对映选择性（diastereoselectivity）与最高99%的对映选择性（enantioselectivity）。