Enantioselectivity in the catalytic hydroesterification of acenaphthylene: Direct evidence of the racemization of Pd<sup>II</sup>-alkyl species by a degenerate substitution equilibrium with Pd<sup>0</sup>L<inf>n</inf>

Jordi Gironyàs, Josep Duran, Alfonso Polo, Julio Real

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19 Citations (Scopus)

Abstract

The palladium catalyzed hydroesterification of acenaphthylene takes place through a “hydride” mechanism, that is, through the selective cis insertion of the olefin into the palladium-hydride bond, an obvious prerequisite for the successful development of an enantioselective version of the reaction; however, a degenerate substitution equilibrium between Pd0Ln and the PdII-alkyl species, involving the inversion of the alkyl carbon, is also operative producing a detrimental effect in the enantioselectivity of the reaction. © 2003 The Royal Society of Chemistry.
Original languageEnglish
Pages (from-to)1776-1778
JournalChemical Communications
Volume3
Issue number14
DOIs
Publication statusPublished - 1 Jan 2003

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