112979-39-2Relevant academic research and scientific papers
One-pot synthesis of β-amino acid derivatives from α-amino acids
Saavedra, Carlos J.,Hernández, Rosendo,Boto, Alicia,álvarez, Eleuterio
, p. 8757 - 8760 (2006)
The one-pot transformation of α-amino acid into β-amino acid derivatives is described. The application of this method to the synthesis of modified dipeptides was also illustrated.
Catalyst-free Mannich-type reaction of 1-(N-acylamino)alkyltriphenylphosphonium salts with silyl enolates
Pa?dzierniok-Holewa, Agnieszka,Wal?cka-Kurczyk, Alicja,Musio?, Szymon,Stecko, Sebastian
, p. 732 - 742 (2019/01/10)
A catalyst-free reaction of 1-(N-acylamino)alkyltriphenylphosphonium tetrafluoroborates with silyl enolates was developed to prepare β-amino carbonyl compounds. The reported method is a useful approach for the preparation of N-protected β-amino esters as
Catalytic, one-pot synthesis of β-amino acids from α-amino acids. Preparation of α,β-peptide derivatives
Saavedra, Carlos,Hernandez, Rosendo,Boto, Alicia,Alvarez, Eleuterio
supporting information; experimental part, p. 4655 - 4665 (2009/10/09)
(Chemical Equation Presented) The one-pot conversion of readily available α-amino acid into β-amino acid derivatives was carried out in good yields. The method is a sequential process initiated by a tandem radical decarboxylation-oxidation reaction; the resulting acyliminium ion was trapped by silyl ketenes. Stoichiometric and catalytic versions of this reaction were developed and then applied to prepare modified di- and tripeptides. Interestingly, some tripeptides formed expanded β-turns in the solid state.
A facile and stereocontrolled synthesis of syn-α-alkyl α-hydroxy β-amino acids
Nocioni, Alessandra Maria,Papa, Carmela,Tomasini, Claudia
, p. 8453 - 8456 (2007/10/03)
The diastereoselective synthesis of syn-α-alkyl α-hydroxy β-amino acids 4a-h was easily accomplished by reaction of the sodium dianion of the corresponding anti α-alkyl β-benzoylamino acid methyl esters with iodine. The intermediate α-iodo derivatives spontaneously afforded cis-oxazolines which, upon hydrolysis, provided the desired products, with diastereoselectivities up to 99:1.
194. Diastereoselecktive Alkylation of 3-Aminobutanoic Acid in the 2-Position
Estermann, Heinrich,Seebach, Dieter
, p. 1824 - 1840 (2007/10/02)
The enantiomerically pure 3-aminobutanoic acids (R)- and (S)-6 are readily available by preparative HPLC separation of the two diastereoisomers 5 obtained from addition of (S)-phenethylamine to methyl crotonate and subsequent hydrogenolysis (Scheme 2). (S)-methyl 3-(benzoylamino)butanoate ((S)-3) is also available by enzymatic kinetic resolution with pig-liver esterase.The N-benzoyl- and N-benzyloxycarbonyl derivatives rac-3, 8,and 9 of 3-aminobutanoates are doubly deprotonated with LDA and alkylated or aminated in high selectivity (17 examples, relative topicity like; see Tables 1 and 2).The configuration of three of the products is assigned (Schemes 4-6), and in four cases, the free α-substituted β-amino acid is prepared by acidic hydrolysis (see Table 3).It is shown that the doubly lithiated β-amino-acid derivative is solubilized, and its reactivity may be strongly influenced by the presence of 3 equiv. of LiCl.
α-ALKYLATION OF β-AMINOBUTANOATES WITH lk-1,2-INDUCTION
Seebach, Dieter,Estermann, Heinrich
, p. 3103 - 3106 (2007/10/02)
Dilithiated methyl- or ethyl-N-benzoyl-3-aminobutanoates are alkylated or added to benzaldehyde to give products of l- and u,u-configuration respectively.Several methods are presented by which enantiomerically pure 3-aminobutanoic derivatives can be prepared.
