New proline analogues for organocatalysis

Dı́ez, David; Antón, Ana B.; Peña, Javier; Garcı́a, Pilar Garcı́a; Garrido, Narciso M.; Marcos, Isidro S.; Sanz, Francisca; Basabe, P.; Urones, Julio G.

doi:10.1016/j.tetasy.2010.05.005

Cited by 11 publications

(4 citation statements)

References 58 publications

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“…With this series of pyrrolidines at hand, the well-established Michael addition of aldehydes to nitroolefins [ 16 – 18 ] was selected as a benchmark reaction to study their behaviour as organocatalysts. Compounds with a related structure prepared from proline by Diez et al have proven to work well as organocatalysts in the Michael addition of cyclohexanones to nitrostyrenes [ 19 – 20 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

Castán¹,

Badorrey²,

Gálvez³

et al. 2017

Beilstein J. Org. Chem.

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New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved.

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Section: Resultsmentioning

confidence: 99%

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

Castán¹,

Badorrey²,

Gálvez³

et al. 2017

Beilstein J. Org. Chem.

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“…128 A reação envolvendo a organocatálise é rápida e os organocatalisadores podem ser facilmente preparados, quando não são disponíveis comercialmente. Outra vantagem é a isenção de metal no produto final, sendo normalmente acompanhadas de elevados valores de rendimento e excesso enantiomérico.…”

Section: Esquema 36 Preparação De Intermediário Para Obtenção Da (L)unclassified

“…Contudo, são necessários novos estudos acerca deste tipo de reação, uma vez que usa grande quantidade de organocatalisador, quando comparada a catálise heterogênea, que utiliza cerca de 0,01% de catalisador. 128 …”

Section: Esquema 36 Preparação De Intermediário Para Obtenção Da (L)unclassified

An Overview of the Different Types of Catalysts in Organic Synthesis

Dias¹,

Ferreira²,

Cunha³

2012

Revista Virtual De Química

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Abstract:Since the mid-twentieth century, by economic and environmental factors, many researchers and some industries are investing in the development of syntheses and technologies that are environmentally friendly, producing less toxic waste and saving energy. Furthermore, the use of renewable raw materials, biomass and the development of asymmetric methods that provide products with high yields and selectivities becomes a major challenge for researchers in various fields that employ the catalytic process. This paper describes the importance of catalysis in organic synthesis of complex molecules, especially for the pharmaceutical and fine chemicals industries. Indeed, the industrial revolution caused by catalysis in different sectors such as petrochemicals, plastics, paper, among others, also became the subject of interest of this review.Keywords: Homogeneous catalysis; heterogeneous catalysis; biocatalysis; organocatalysis. ResumoDesde meados do século XX, por razões econômicas e ambientais, diversos pesquisadores e algumas indústrias investem no desenvolvimento de tecnologias sintéticas que sejam ambientalmente favoráveis, gerando menos resíduos tóxicos e com economia de energia. Além disso, os processos catalíticos e biocatalíticos associados ao uso de biomassas renováveis são de fundamental importância para a produção de matérias-primas quirais e aquirais com altos rendimentos e elevadas seletividades. Esse conjunto de paradigmas é um dos grandes desafios da atualidade para os pesquisadores nos diversos ramos da síntese orgânica.Este trabalho descreve a importância da catálise e da biocatálise na síntese orgânica de moléculas complexas, destacando-se os setores de química fina e fármacos. Além disso, a utilização crescente dos diversos processos catalíticos em diferentes setores industriais, tais como petroquímico, de papel e celulose, plásticos, e muitos outros também são assuntos de interesse desse trabalho de revisão.Palavras-chave: Catálise homogênea; catálise heterogênea; biocatálise; organocatálise.

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“…Later, Headley et al described the synthesis of pyrrolidine-based pyridinium ionic liquids for asymmetric Michael reaction [30]. Last year, novel pyrrolidine-based chiral ionic liquids and other pyrrolidine analogues were synthesized and applied for asymmetric organic reactions, especially for Michael addition [31][32][33]. We designed a new chiral ionic liquids of the structure similar to described in literature [19] but with different alkyl substituents incorporated to imidazolium ring and anions [Formula (I)-(IV)] as catalysts for asymmetric synthesis.…”

Section: Introductionmentioning

confidence: 99%

Ionic liquids as the catalysts for asymmetric reactions

Dąbrowski¹,

Wiśniewska²,

Kulig-Adamiak³

et al. 2012

Polimery

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Ionic liquids as the catalysts for asymmetric reactionsSummary -A new 7 functionalized chiral ionic liquids (CILs) based on pyrrolidine have been synthesized from (S)-proline as a main substrat. The obtained compounds have 1-[(S)-(pyrrolidin-2-yl)methyl]-3-alkylimidazolium cation and bis(trifluoromethylsulfonyl)imide and hexafluorophosphate anions. The structures of the obtained catalysts were determined by spectroscopic analysis 1 H NMR, 13 C NMR and 19 F NMR. This chiral ionic liquids have been applied as efficient catalysts for Michael addition of cyclohexanone to nitroalkenes.

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New proline analogues for organocatalysis

Cited by 11 publications

References 58 publications

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

An Overview of the Different Types of Catalysts in Organic Synthesis

Ionic liquids as the catalysts for asymmetric reactions

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