Gladiali, Serafino Gabriele and Taras, Rossana and Ceder, Rosa M. and Rocamora, Mercè and Muller, Guillermo and Solans, Xavier and Font-Bardia, Mercè (2004) Asymmetric allylic alkylation catalyzed by Pd(II)-complexes with (S)-BINPO, a hemilabile axially chiral P, O-heterodonor inducer. Tetrahedron: Asymmetry, Vol. 15 (9), p. 1477-1485. ISSN 0957-4166. Article.
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A complex generated in situ from [Pd(η3-C3H5)Cl]2 and (S)-BINPO 1 is an active catalyst in the asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl esters 6 via a malonate anion with ee's up to 81% being obtained. Rate and stereoselectivity of the reaction are dramatically influenced by the solvent. The Pd-complex [(S)-(BINPO)Pd(η3-1,3-diphenylallyl)] 5has been synthesized and its structure in the solid state determined by X-ray diffraction. The stoichiometric reaction of 5 with malonate anion affords the alkylated product of the same configuration as the one obtained in the catalytic reaction at room temperature in nearly identical enantiomeric purity (71%).
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