Stereoselective synthesis of γ-amino acids

Enzymatic Method for the Synthesis of Blockbuster Drug Intermediates – Synthesis of Five‐Membered Cyclic γ‐Amino Acid and γ‐Lactam Enantiomers

“…[2] (In this specification, the following numbering and nomenclature are applied for the compounds: cis-4-aminocyclopent-2-ene-1-carboxylic acid and its (1S,4R)-(-) and (1R,4S)-(+) enantiomers, cis-3-aminocyclopentane-1-carboxylic acid, 2-azabicyclo[2.2.1]hept-5-en-3-one and 2-azabicyclo[2.2.1]heptan-3-one. )…”

Concise Pathway to New Multifunctionalized Constrained Pentacin Derivatives by Means of Two Stereospecific Tandem Reactions

“…[9] Although numerous substituted derivatives of alicyclic α-and γ-amino acids have been synthesized and extensively studied for their biological properties, [10,11] β-derivatives have been investigated only in a limited number of cases [12] and mainly for their ability to form original structures. [13][14][15][16][17][18][19] In the cyclopentanic series, a more specific concern has been dedicated to alkyl derivatives, [20,21] aminated [22] and/or hydroxylated analogues, [22][23][24][25][26][27] which is certainly correlated with the structure of the antibiotic oryzoxymicin.…”

Enantioselective Organocatalytic Michael Addition of Aldehydes to Nitroethylene: Efficient Access to γ2-Amino Acids

“…9 The preparation of enantiomerically pure γ-amino acids is challenging, and this synthetic burden has limited the study of γ-peptide foldamers to date. A variety of routes to enantioenriched γ 2 -amino acids have been described, 10 but these approaches often involve specialized chiral auxiliaries and may not be ideal for preparing multigram quantities of protected γ 2 -amino acids bearing diverse side chain functionality, which is necessary for foldamer research. 6,7 Here we report an asymmetric organocatalytic method for aminoethylation of aldehydes, which leads to a new and efficient synthesis of γ 2 -amino acids (Scheme 1).…”

“…We have shown that such intermediates can be converted expeditiously to protected γ 2 -amino acids, which are interesting as foldamer building blocks. Relatively few methods have been previously described for γ 2 -amino acid synthesis, 10 and these approaches might be challenging to apply to examples featuring diverse side chain functionality. Mechanistic studies regarding the role of acid co-catalyst and the catalytic pathway are in progress.…”