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Fine-Tuning Monophosphine Ligands for Enhanced Enantioselectivity. Influence of Chiral Hemilabile Pendant Groups

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journal contribution
posted on 2004-04-29, 00:00 authored by Aibin Zhang, T. V. RajanBabu
C2-Symmetric P-(2-X-aryl)-2,5-dialkylphospholanes (X = dioxolan-2-yl or dioxan-2-yl), designed on the basis of a working model for asymmetric induction, are effective ligands for the Ni(II)-catalyzed asymmetric hydrovinylation of styrenes. Excellent yields (>99%), selectivities for the desired 3-arylbutenes (>99%), high S/C ratios (>1200), and ee's (up to 91%) have been realized for a number of prototypical vinylarenes. In the dioxolane series, the selectivity depends on the configuration of the C4 and C5 carbons.