Pyranoside phosphite–phosphoroamidite ligands for Pd-catalyzed asymmetric allylic alkylation reactions |
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Affiliation: | 1. G.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, Ivanovo 153045, Russia;2. Department of Chemistry, Moscow State University, Moscow 119899, Russia |
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Abstract: | We have designed and synthesized a new family of readily available phosphite–phosphoroamidite ligands for Pd-catalyzed allylic substitution reactions of several substrates with different steric and electronic properties. These ligands are derived from d-glucosamine and contain several substituents in the biphenyl moieties, with different steric and electronic properties. Systematic variation of the ligand parameters indicates that enantioselectivities are mainly affected by the substituents at the para-positions of the biphenyl moieties. Enantiomeric excesses of up to 89% with high activities were obtained for rac-1,3-diphenyl-3-acetoxyprop-1-ene S1, rac-(E)-ethyl-2,5-dimethyl-3-hex-4-enylcarbonate S2 and rac-3-acetoxycycloheptene S5. |
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