475598-30-2Relevant academic research and scientific papers
Synthesis of novel amino acids and dehydroamino acids containing the benzo[b]thiophene moiety
Abreu, Ana S.,Silva, Natalia O.,Ferreira, Paula M. T.,Queiroz, Maria-Joao R. P.
, p. 1537 - 1544 (2007/10/03)
Several novel amino acids and dehydroamino acids containing the benzo[b]thiophene moiety were prepared by Michael addition or sequential Michael addition and palladium-catalyzed C-C or C-N cross couplings. The substrates for Michael addition were the methyl esters of N,N-bis(tertbutyloxycarbonyl)dehydroalanine [Boc2-ΔAla-OMe] and N-(4-toluenesulfonyl)-N-(tert-butyloxycarbonyl)dehydroalanine [Tos-ΔAla(N-Boc)-OMe], and the nucleophiles were aromatic thiols and 3-iodobenzylamine. The addition of mercaptobenzo[b]thiophenes directly to Tos-ΔAla(N-Boc)-OMe gave stereoselectively, in good yields, the E-isomer of the corresponding dehydrocysteine. When thiophenols and 3-iodobenzylamine were used as nucleophiles the presence of an additional function (halogen or amine) allowed a subsequent palladium-catalyzed cross-coupling reaction with functionalized benzo[b]thiophenes (boronic acids, a halogen or an amine). Using this strategy, several racemic amino acid and dehydroamino acid derivatives, which are linked to the benzo[b]thiophene moiety by an aromatic spacer, were obtained in good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Synthesis of non-proteinogenic amino acids from N-(4-toluenesulfonyl)dehydroamino acid derivatives
Ferreira, Paula M.T.,Maia, Hernani L.S.,Monteiro, Luís S.
, p. 4495 - 4497 (2007/10/03)
By treating N-(4-toluenesulfonyl)-N-(tert-butyloxycarbonyl)-dehydroamino acid derivatives with different reactants under different conditions, a variety of new amino acids are obtained, viz. (i) α-alcoxy-α-amino acids, (ii) α,α-diamino acids and (iii) novel β-substituted dehydroamino acids.
