Construction of Chiral Isotetronic Acid-Fused Thiochromane via Doubly Annulative Strategy.

A sulfa-Michael/aldol/lactonization cascade reaction has been established to construct isotetronic acid-fused thiochromanes in a highly stereoselective fashion (≥11:1 dr, 35-98% ee). The tricyclic products were obtained in 35-99% isolated yields in the presence of a bifunctional squaramide. Three reactive sites of β,γ-unsaturated α-ketoester, including the less-explored ester carbonyl group, were sequentially utilized to construct two fused heterocycles in a one-pot operation.

Highly stereoselective synthesis of 2,3-dihydrofurans via a cascade Michael addition-alkylation process: a nitro group as the leaving group.

The Michael addition-alkylation process between gem-benzoyl-nitrostyrenes and 1,3-dicarbonyl compounds proceeded smoothly in the presence of a bifunctional squaramide, exclusively providing 2,3-dihydrofurans as trans-diastereomers in 33-92% isolated yields and excellent enantioselectivities (29->99% ee).