About: Opportunities offered by chiral éta6-arene/N-arylsulfonyl-diamine-Ru(II) catalysts in the asymmetric transfer hydrogenation of ketones and imines     Goto   Sponge   NotDistinct   Permalink

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  • A review. Methods for the asym. transfer hydrogenation (ATH) of ketones and imines were intensively studied and developed. Of foremost interest is the use of Noyori's [RuCl(éta6-arene)(N-TsDPEN)] complexes in the presence of a hydrogen donor (i-PrOH, formic acid). These complexes found numerous practical applications and were extensively modified. The resulting derivs. were heterogenized, used in ATH in water or ionic liqs. and even some attempts were made to approach the properties of biocatalysts. Therefore, an appropriate modification of the catalyst that suits the specific requirements for the reaction conditions is very often readily available. The mechanism of the reaction was also explored to a great extent. Model substrates, acetophenone (a ketone) and 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline (an imine), are both reduced by this Ru catalytic system with almost perfect selectivity. However, in each case the major product is a different enantiomer (S - for an alc., R - for an amine when the S,S-catalyst is used), which demanded an in-depth mechanistic investigation. Full-scale mol. modeling of this system enabled us to visualize the plausible 3D structures of the transition states, allowing the proposition of a viable explanation of previous exptl. findings.
  • A review. Methods for the asym. transfer hydrogenation (ATH) of ketones and imines were intensively studied and developed. Of foremost interest is the use of Noyori's [RuCl(éta6-arene)(N-TsDPEN)] complexes in the presence of a hydrogen donor (i-PrOH, formic acid). These complexes found numerous practical applications and were extensively modified. The resulting derivs. were heterogenized, used in ATH in water or ionic liqs. and even some attempts were made to approach the properties of biocatalysts. Therefore, an appropriate modification of the catalyst that suits the specific requirements for the reaction conditions is very often readily available. The mechanism of the reaction was also explored to a great extent. Model substrates, acetophenone (a ketone) and 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline (an imine), are both reduced by this Ru catalytic system with almost perfect selectivity. However, in each case the major product is a different enantiomer (S - for an alc., R - for an amine when the S,S-catalyst is used), which demanded an in-depth mechanistic investigation. Full-scale mol. modeling of this system enabled us to visualize the plausible 3D structures of the transition states, allowing the proposition of a viable explanation of previous exptl. findings. (en)
Title
  • Opportunities offered by chiral éta6-arene/N-arylsulfonyl-diamine-Ru(II) catalysts in the asymmetric transfer hydrogenation of ketones and imines
  • Opportunities offered by chiral éta6-arene/N-arylsulfonyl-diamine-Ru(II) catalysts in the asymmetric transfer hydrogenation of ketones and imines (en)
skos:prefLabel
  • Opportunities offered by chiral éta6-arene/N-arylsulfonyl-diamine-Ru(II) catalysts in the asymmetric transfer hydrogenation of ketones and imines
  • Opportunities offered by chiral éta6-arene/N-arylsulfonyl-diamine-Ru(II) catalysts in the asymmetric transfer hydrogenation of ketones and imines (en)
skos:notation
  • RIV/60461373:22310/11:43891934!RIV12-MSM-22310___
http://linked.open...avai/predkladatel
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(GA104/09/1497), Z(MSM6046137301)
http://linked.open...iv/cisloPeriodika
  • 7
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 218505
http://linked.open...ai/riv/idVysledku
  • RIV/60461373:22310/11:43891934
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • molecular modelling; chiral; ketones; imines; asymmetric transfer hydrogenation (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • CH - Švýcarská konfederace
http://linked.open...ontrolniKodProRIV
  • [045539D068A4]
http://linked.open...i/riv/nazevZdroje
  • Molecules
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
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http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 16
http://linked.open...iv/tvurceVysledku
  • Kačer, Petr
  • Kuzma, Marek
  • Václavík, Jiří
  • Červený, Libor
http://linked.open...ain/vavai/riv/wos
  • 000293073900011
http://linked.open...n/vavai/riv/zamer
issn
  • 1420-3049
number of pages
http://bibframe.org/vocab/doi
  • 10.3390/molecules16075460
http://localhost/t...ganizacniJednotka
  • 22310
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