Stereoselective Synthesis of Dihydrofuranoindoles via the Friedel-Crafts Alkylation/Annulation Cascade Process
Xiaodi Dong1, Zhishun Tang1, Ling Ye2
1College of Chemistry and Environment Protection Engineering, Southwest Minzu University, Chengdu 610041, China.
Abstract:
A stereoselective annulation protocol was developed to construct dihydrofuranoindoles from readily available starting materials. In the presence of a bifunctional squaramide, the Friedel-Crafts alkylation/annulation cascade process occurred smoothly to provide dihydrofuranoindoles in 26-95% isolated yields exclusively as trans-diastereomers (38-99% ee). This catalytic protocol was compatible with a range of structurally distinct hydroxyindoles bearing the hydroxyl group at different positions, providing four kinds of dihydrofuranoindoles. Moreover, gram-scale synthesis and further synthetic manipulation of the product were also demonstrated.
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