title: Preparation of conformationally restricted β(2,2)- and β(2,2,3)-amino esters and derivatives containing an all-carbon quaternary center.
abstract: β-Amino acids are routinely incorporated into peptidic drugs to increase their stability and to incur conformational biases. However, the synthesis of highly substituted β-amino acids still represents a great challenge. A new approach to their preparation is reported involving a Vilsmeier-Haack reaction with nonaromatic carbon nucleophiles. The highly challenging preparation of contiguous tertiary and all-carbon quaternary centers was successfully used to generate several β(2,2,3)-amino esters, such as derivatives of homoproline, homoalanine, and homopipecolinic esters.
authors.affiliation: Département de Chimie, Université de Sherbrooke , 2500 boulevard de l'Université, Sherbrooke, Québec J1K 2R1, Canada.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Romanens
authors.forename: Guillaume
authors.initials: G
authors.lastname: Bélanger
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D000613:Aminobutyrates / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D004952:Esters; D008968:Molecular Conformation; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000613:Aminobutyrates; D004952:Esters; D010875:Pipecolic Acids; D002244:Carbon; C012223:alpha-aminobutyric acid; D011392:Proline; C010983:homoproline; C031345:pipecolic acid