Sterically congested, "roofed" β-iminodisulfides as new chiral ligands for palladium-catalyzed, asymmetric allylic alkylation.

The preparation of a new class of “roofed” β-iminodisulfides from sterically congested, conformationally rigid chiral 2-thiazolidinones is described. A functional survey of palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate proved that symmetrical “roofed” β-iminodisulfides are efficient chiral ligands, showing enantioselectivity opposite that associated with chiral “roofed” β-iminothioether ligands.