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Communication | Special issue | Vol 66, No. 1, 2005, pp.135-141
Published online, 28th October, 2005
DOI: 10.3987/COM-05-S(K)50
Sterically Congested “Roofed” 2-Iminothioethers as New Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation

Ryoh Tokuda, Hirofumi Matsunaga,* Tadao Ishizuka, Makoto Nakajima, and Takehisa Kunieda*

*Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan

Abstract

The preparation of a new class of “roofed” aminothiol derivatives, from sterically congested, conformationally rigid chiral 2-thiazolidinones is described. The compounds function as efficient chiral ligands for the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate in the presence of cesium carbonate as a base.