Temperature dependence of the asymmetric induction in the PtCl(SnCl3)[(-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane]-catalyzed enantioselective hydroformylation reaction

L. Kollár, J. Bakos, Imre Tóth, Bálint Heil

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Abstract

Asymmetric hydroformylation of some prochiral olefins has been shown to be catalyzed by a new (preformed) PtCl(SnCl3)[(S,S)-BDPP] ((S,S)-BDPP = (-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane) catalyst. Vinylidene carboxylic esters are hydroformylated regioselectively but with rather moderate enantioselectivity. In hydroformylation of styrene the linear non chiral regioisomer 3-phenylpropanal is the main product, but the enantioselective formation of 2-phenylpropanal is strongly influenced by the reaction temperature, The S-enantiomer predominate at lower and the R-species at higher temperatures. Appropriate choices of the partial pressure of CO and H2 led to a relatively high (76.5%) enantiomeric excess.

Original languageEnglish
Pages (from-to)277-284
Number of pages8
JournalJournal of Organometallic Chemistry
Volume350
Issue number2
DOIs
Publication statusPublished - Aug 9 1988

Fingerprint

Hydroformylation
pentanes
enantiomers
vinylidene
styrenes
alkenes
partial pressure
esters
induction
catalysts
temperature dependence
Temperature
Styrene
Enantiomers
Partial Pressure
Enantioselectivity
Alkenes
Carbon Monoxide
products
Partial pressure

ASJC Scopus subject areas

  • Biochemistry
  • Chemical Engineering (miscellaneous)
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Science (miscellaneous)
  • Materials Chemistry

Cite this

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title = "Temperature dependence of the asymmetric induction in the PtCl(SnCl3)[(-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane]-catalyzed enantioselective hydroformylation reaction",
abstract = "Asymmetric hydroformylation of some prochiral olefins has been shown to be catalyzed by a new (preformed) PtCl(SnCl3)[(S,S)-BDPP] ((S,S)-BDPP = (-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane) catalyst. Vinylidene carboxylic esters are hydroformylated regioselectively but with rather moderate enantioselectivity. In hydroformylation of styrene the linear non chiral regioisomer 3-phenylpropanal is the main product, but the enantioselective formation of 2-phenylpropanal is strongly influenced by the reaction temperature, The S-enantiomer predominate at lower and the R-species at higher temperatures. Appropriate choices of the partial pressure of CO and H2 led to a relatively high (76.5{\%}) enantiomeric excess.",
author = "L. Koll{\'a}r and J. Bakos and Imre T{\'o}th and B{\'a}lint Heil",
year = "1988",
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journal = "Journal of Organometallic Chemistry",
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TY - JOUR

T1 - Temperature dependence of the asymmetric induction in the PtCl(SnCl3)[(-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane]-catalyzed enantioselective hydroformylation reaction

AU - Kollár, L.

AU - Bakos, J.

AU - Tóth, Imre

AU - Heil, Bálint

PY - 1988/8/9

Y1 - 1988/8/9

N2 - Asymmetric hydroformylation of some prochiral olefins has been shown to be catalyzed by a new (preformed) PtCl(SnCl3)[(S,S)-BDPP] ((S,S)-BDPP = (-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane) catalyst. Vinylidene carboxylic esters are hydroformylated regioselectively but with rather moderate enantioselectivity. In hydroformylation of styrene the linear non chiral regioisomer 3-phenylpropanal is the main product, but the enantioselective formation of 2-phenylpropanal is strongly influenced by the reaction temperature, The S-enantiomer predominate at lower and the R-species at higher temperatures. Appropriate choices of the partial pressure of CO and H2 led to a relatively high (76.5%) enantiomeric excess.

AB - Asymmetric hydroformylation of some prochiral olefins has been shown to be catalyzed by a new (preformed) PtCl(SnCl3)[(S,S)-BDPP] ((S,S)-BDPP = (-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane) catalyst. Vinylidene carboxylic esters are hydroformylated regioselectively but with rather moderate enantioselectivity. In hydroformylation of styrene the linear non chiral regioisomer 3-phenylpropanal is the main product, but the enantioselective formation of 2-phenylpropanal is strongly influenced by the reaction temperature, The S-enantiomer predominate at lower and the R-species at higher temperatures. Appropriate choices of the partial pressure of CO and H2 led to a relatively high (76.5%) enantiomeric excess.

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U2 - 10.1016/0022-328X(88)80383-8

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JF - Journal of Organometallic Chemistry

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