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Synthesis of fluorescent alanines by a rhodium catalysed conjugate addition of ...

Ferreira, Paula M. T.; Monteiro, Luís S.; Castanheira, Elisabete M. S.; Pereira, Goreti; Frost, Christopher G.

Several arylalanine derivatives containing fluorescent groups were prepared in good yields using a rhodium catalysed conjugate addition of arylboronic acids to N,N-diprotected and N-monoprotected dehydroalanines. The best conditions for these reactions require the use of an excess of aryl boronic acid (4 equiv.), [Rh(COD)2]BF4 as catalyst and CsF as base in dioxane:H2O (10:1) at 110 ºC. These conditions were al...


Synthesis of new n-ethyl dehydroamino acids

Monteiro, Luís S.; Suárez, Ana C.; Andrade, Juliana J.


High yielding synthesis of N-ethyl dehydroamino acids

Monteiro, Luís S.; Suárez, Ana C.

Recently we reported the use of a sequence of alkylation and dehydration methodologies to obtain N-ethyl-α, β-dehydroamino acid derivatives. The application of this N-alkylation procedure to several methyl esters of β, β-dibromo and β--bromo, β-substituted dehydroamino acids protected with standard amine protecting groups was subsequently reported. The corresponding N-ethyl, β-bromo dehydroamino acid derivative...


Synthesis of new n-ethyl dehydroamino acid derivatives : n-ethyl β,β-dibromo, n...

Monteiro, Luís S.; Andrade, Juliana J.; Suárez, Ana C.

Recently we reported the use of a sequence of alkylation and dehydration methodologies to obtain from the methyl esters of N-(4-nitrophenylsulfonyl)-β-hydroxyamino acids, new non-proteinogenic amino acids, namely, N-ethyl-α,β-dehydroamino acids. Thus, it was possible to obtain for the first time, non-natural amino acids which incorporate both the N-ethyl and α,β-dehydro moieties. Herein, we report the applicati...


Electrochemical reduction of dehydroamino acids: Synthesis and photophysical pr...

Ferreira, Paula M. T.; Monteiro, Luís S.; Castanheira, Elisabete M. S.; Pereira, Goreti; Lopes, Carla; Vilaça, Helena

Several beta,beta-disubstituted dehydroalanines were prepared from beta,beta-dibromo or beta-bromo, beta-substituted dehydroalanines and aryl boronic acids using a Suzuki-Miyaura cross-coupling reaction. The electrochemical behaviour of these compounds was studied by cyclic voltammetry. All compounds studied showed similar reduction potentials and these were similar to the peak potential of the methyl ester of ...


High yielding synthesis of oxazole-4-carboxylates from dehydroamino acid deriva...

Pereira, Goreti; Castanheira, Elisabete M. S.; Ferreira, Paula M. T.; Monteiro, Luís S.; Vilaça, Helena


Electrochemical reduction of β-Aryldehydroamino acid derivatives

Ferreira, Paula M. T.; Monteiro, Luís S.; Castanheira, Elisabete M. S.; Pereira, Goreti; Lopes, Carla


Synthesis of novel non-proteinogenic amino acids : n-ethyl-alpha, beta-dehydroa...

Monteiro, Luís S.; Kołomańska, Joanna; Suárez, Ana C.


Synthesis of new chemosensors for fluoride ion from dehydroamino acid derivatives

Pereira, Goreti; Castanheira, Elisabete M. S.; Ferreira, Paula M. T.; Monteiro, Luís S.; Queiroz, Maria João R. P.


Pyrenylamino acids : synthesis, photophysical and electrochemical studies

Abreu, Ana S.; Castanheira, Elisabete M. S.; Ferreira, Paula M. T.; Monteiro, Luís S.; Pereira, Goreti; Queiroz, Maria João R. P.

Several beta-pyrenyldehydroamino acids and a pyrenylalanine derivative were synthesized in good to high yields from dehydroamino acids using several types of reactions. A beta-[(pyren-1-yl)methylamino]alanine was prepared treating the methyl ester of N,N-(di-tert-butoxycarbonyl)dehydroalanine with 1-pyrenemethylamine hydrochloride in the presence of an excess of potassium carbonate. The methyl esters of N-(tert...


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Fundação para a Ciência e a Tecnologia Universidade do Minho   Governo Português Ministério da Educação e Ciência Programa Operacional da Sociedade do Conhecimento União Europeia