title: Synthesis of arylglycine and mandelic acid derivatives through carboxylations of α-amido and α-acetoxy stannanes with carbon dioxide.
abstract: Incorporation reactions of carbon dioxide (CO(2)) with N-Boc-α-amido and α-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected α-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO(2) pressure. α-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO(2) pressure. Both transformations enabled the synthesis of α-tertiary and α-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-α-amido stannanes was transferred with up to 90% inversion of configuration at 100 °C.
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. tmita@pharm.hokudai.ac.jp
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Mita
authors.forename: Masumi
authors.initials: M
authors.lastname: Sugawara
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Hasegawa
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Sato
mesh_terms: D002245:Carbon Dioxide / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008333:Mandelic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry*
chemical_list: D008333:Mandelic Acids; D017971:Tin Compounds; D002245:Carbon Dioxide; C031525:stannane; C037938:mandelic acid; D005998:Glycine