83460-81-5Relevant academic research and scientific papers
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.
Synthesis of β-Amino-acid Peptides. Part 3. Preparation of Racemic and Chiral 3-Aminobutyric Acid Derivatives and Peptides Using Dihydrooxazin-6-ones and Conventional Coupling Reagents
Drey, Charles N. C.,Mtetwa, Eli
, p. 1587 - 1592 (2007/10/02)
Peptides of R,S and S-3-aminobutyric acid have been prepared by conventional methods and also by using chiral oxazin-6-ones, the latter method proving to be superior because of the absence of the side-reactions.S-3-Aminobutyric acid derivatives were prepared by Arndt-Eistert homologation.
