title: One-step synthesis of racemic α-amino acids from aldehydes, amine components, and gaseous CO2 by the aid of a bismetal reagent.
abstract: α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid can be divided into three basic components: an aldehyde, an amine, and carbon dioxide (CO(2)). We report herein that a one-step synthesis of α-amino acids has been successfully achieved from these three basic and inexpensive chemicals with a single operation, in which the mixture of an aldehyde, a sulfonamide, and gaseous CO(2) was heated at 100 °C in the presence of Bu(3)Sn-SnBu(3) and CsF. In this one-pot sequential protocol, two important intermediates (imine and α-amino stannane) are involved and the stannyl anion generated in situ plays a crucial role, particularly for the efficient stannylation of the imine in the presence of proton sources and for promoting retrostannylation of the undesired α-alkoxy stannane owing to its high stability and tolerance of the presence of proton sources. This methodology enabled the synthesis of a wide range of racemic arylglycine derivatives in high yields.
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Nishi 6, Kita 12, Kita-ku, Sapporo 060-0812, Japan. tmita@pharm.hokudai.ac.jp
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Mita
authors.forename: Yuki
authors.initials: Y
authors.lastname: Higuchi
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Sato
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002245:Carbon Dioxide / Q000737:chemistry*; D002586:Cesium / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D000596:Amino Acids; D009947:Organotin Compounds; D002245:Carbon Dioxide; D002586:Cesium; D005459:Fluorides; C027754:cesium fluoride