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Communication | Special issue | Vol 50, No. 1, 1999, pp.89-94
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)64
(S)-Proline-derived Chiral Ligands Bearing Organosulfur or -selenenyl Groups as Coordinating Elements in Palladium-catalyzed Asymmetric Allylic Alkylations

Yoshio Suzuki, Ikuko Abe, and Kunio Hiroi*

*Department of Synthetic Organic Chemistry, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

(S)-Proline-derived chiral ligands bearing organosulfur or -selenenyl groups as coordinating elements were synthesized, and applied to palladium-catalyzed asymmetric allylic alkylations. These heteroatoms in the ligands played a prominent role for the stereocontrol of the conformation of the intermediary palladium complexes, and resulting for the presentation of the high asymmetric induction in the asymmetric alkylations. The mechanism of the asymmetric synthesis using these ligands is rationalized on the basis of stereochemical outcome observed.