Polystyrene-supported organocatalysts for alfa-selenenylation and Michael reactions. A common post-modification approach for catalytic differentiation

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Abstract

Three different resin-supported catalysts have been prepared by using the well established post-modification approach by means of thiol-ene coupling reaction. Two catalysts were tested for the first time in the asymmetric α-selenenylation of propanal, while the third catalyst was used in the Michael addition reaction. While the preliminary results are not encouraging in the case of supported Jørgensen’ catalyst, interesting data have been collected with both for the supported MacMillan and prolyl-prolinol catalysts. In fact, these catalysts displayed good activity and selectivity. A reversed enantioselectivity in the α-selenenylation was observed by changing the polarity of the solvent. Finally, these materials were easily recovered, and used four and five times, respectively.
Lingua originaleEnglish
pagine (da-a)75-80
Numero di pagine6
RivistaDefault journal
Volume16
Stato di pubblicazionePublished - 2011

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Polystyrenes
Catalysts
Catalyst supports
Addition reactions
Catalyst selectivity
Enantioselectivity
Sulfhydryl Compounds
Catalyst activity
Resins

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Process Chemistry and Technology
  • Chemistry(all)

Cita questo

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title = "Polystyrene-supported organocatalysts for alfa-selenenylation and Michael reactions. A common post-modification approach for catalytic differentiation",
abstract = "Three different resin-supported catalysts have been prepared by using the well established post-modification approach by means of thiol-ene coupling reaction. Two catalysts were tested for the first time in the asymmetric α-selenenylation of propanal, while the third catalyst was used in the Michael addition reaction. While the preliminary results are not encouraging in the case of supported J{\o}rgensen’ catalyst, interesting data have been collected with both for the supported MacMillan and prolyl-prolinol catalysts. In fact, these catalysts displayed good activity and selectivity. A reversed enantioselectivity in the α-selenenylation was observed by changing the polarity of the solvent. Finally, these materials were easily recovered, and used four and five times, respectively.",
keywords = "Michael reaction, alfa-selenenylation, organocatalysis, supported catalysts",
author = "Renato Noto and Vincenzo Campisciano and Francesco Giacalone and Michelangelo Gruttadauria and Paola Agrigento",
year = "2011",
language = "English",
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T1 - Polystyrene-supported organocatalysts for alfa-selenenylation and Michael reactions. A common post-modification approach for catalytic differentiation

AU - Noto, Renato

AU - Campisciano, Vincenzo

AU - Giacalone, Francesco

AU - Gruttadauria, Michelangelo

AU - Agrigento, Paola

PY - 2011

Y1 - 2011

N2 - Three different resin-supported catalysts have been prepared by using the well established post-modification approach by means of thiol-ene coupling reaction. Two catalysts were tested for the first time in the asymmetric α-selenenylation of propanal, while the third catalyst was used in the Michael addition reaction. While the preliminary results are not encouraging in the case of supported Jørgensen’ catalyst, interesting data have been collected with both for the supported MacMillan and prolyl-prolinol catalysts. In fact, these catalysts displayed good activity and selectivity. A reversed enantioselectivity in the α-selenenylation was observed by changing the polarity of the solvent. Finally, these materials were easily recovered, and used four and five times, respectively.

AB - Three different resin-supported catalysts have been prepared by using the well established post-modification approach by means of thiol-ene coupling reaction. Two catalysts were tested for the first time in the asymmetric α-selenenylation of propanal, while the third catalyst was used in the Michael addition reaction. While the preliminary results are not encouraging in the case of supported Jørgensen’ catalyst, interesting data have been collected with both for the supported MacMillan and prolyl-prolinol catalysts. In fact, these catalysts displayed good activity and selectivity. A reversed enantioselectivity in the α-selenenylation was observed by changing the polarity of the solvent. Finally, these materials were easily recovered, and used four and five times, respectively.

KW - Michael reaction

KW - alfa-selenenylation

KW - organocatalysis

KW - supported catalysts

UR - http://hdl.handle.net/10447/60065

M3 - Article

VL - 16

SP - 75

EP - 80

JO - Default journal

JF - Default journal

ER -