title: Enantioselective Synthesis of Quaternary α-Amino Acids Enabled by the Versatility of the Phenylselenonyl Group.
abstract: A novel Cinchona alkaloid-catalyzed enantioselective conjugate addition of α-alkyl substituted α-nitroacetates to phenyl vinyl selenone was developed. The resulting enantio-enriched α,α-dialkyl substituted α-nitroacetates were subsequently converted to various cyclic and acyclic quaternary α-amino acids, taking advantage of the rich functionalities of the resulting Michael adducts. Novel protocols allowing chemoselective reduction of phenyl selenone to phenyl selenide and reduction of alkyl phenyl selenones to alkanes are also reported.
authors.affiliation: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
authors.forename: Antonin
authors.initials: A
authors.lastname: Clemenceau
authors.affiliation: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.affiliation: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D018036:Selenium Compounds / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D002930:Cinchona Alkaloids; D018036:Selenium Compounds
keywords: asymmetric synthesis; nitroacetate; organocatalysis; quaternary amino acid; selenium