Abstract

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.

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