2014
DOI: 10.1021/om401104g
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Influence of the 4-Substituents on the Reversal of Enantioselectivity in the Asymmetric Hydroformylation of 4-Substituted Styrenes with PtCl(SnCl3)[(2S,4S)-BDPP]

Abstract: The enantioselectivity of the asymmetric hydroformylation of 4-substituted styrenes in the presence of an in situ catalyst, formed from PtCl(SnCl 3 )[(2S,4S)-BDPP] and tin(II) chloride, was influenced by the reaction temperature. The preferred formation of the S and the R enantiomers of the branched aldehyde regioisomers (2a−g) was observed at low and high temperatures, respectively. The electron-donor or electron-acceptor properties of the para substituents of styrene show correlation with the changes in enan… Show more

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Cited by 17 publications
(5 citation statements)
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“…Recent computational studies by Kégl and co-workers about the influence of the electronic properties of the substituents in the phenyl group of p -substituted styrenes in the enantioselectivity of these hydroformylations have been performed. They showed an excellent linear correlation of the p -substituents Hammet constants and the electrostatic potential at nuclei of the Pt atom as well as in the coordination sphere of Pt . In the case of electron-donating substituents, a reversal of enantioselectivity was observed at lower temperature than with styrenes containing electron-withdrawing substituents.…”
Section: Stereodivergence In Acyclic Systemsmentioning
confidence: 99%
“…Recent computational studies by Kégl and co-workers about the influence of the electronic properties of the substituents in the phenyl group of p -substituted styrenes in the enantioselectivity of these hydroformylations have been performed. They showed an excellent linear correlation of the p -substituents Hammet constants and the electrostatic potential at nuclei of the Pt atom as well as in the coordination sphere of Pt . In the case of electron-donating substituents, a reversal of enantioselectivity was observed at lower temperature than with styrenes containing electron-withdrawing substituents.…”
Section: Stereodivergence In Acyclic Systemsmentioning
confidence: 99%
“…20). 167 The electrostatic potential at nuclei (EPN) was chosen as quantum chemical descriptor which is dened according to eqn (3).…”
Section: Hydroformylation By Platinum Containing Systemsmentioning
confidence: 99%
“…11,12 A katalitikusan aktív rendszer teljes mûködési tartományában végzett vizsgálatokból kiderült, hogy a (2S,4S)-bdpp-t tartalmazó katalizátorral alacsony hõmérsékleten az (S)-2 fenil-propanal, magasabb hõmérsékleten pedig annak (R)-enantiomerje képzõdik nagyobb mennyiségben (10. Ábra).…”
Section: áBra Az óN(ii)-klorid Szerepének Vizsgálata Hp Nmr Segítségévelunclassified