title: Role of the countercation in diastereoselective alkylations of pyramidalized bicyclic serine enolates. An easy approach to alpha-benzylserine.
abstract: The use of a chiral serine equivalent as an excellent chiral building block has been demonstrated in the synthesis of alpha-benzylserine through a diastereoselective lithium enolate alkylation reaction and subsequent acid hydrolysis. The role of a coordinating countercation (lithium) in the alkylation reaction has been investigated. Theoretical studies have been performed in order to elucidate the stereochemical outcome of the alkylation process, which occurs with total retention of configuration.
authors.affiliation: Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, UA-CSIC, 26006 Logroño, Spain.
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Jiménez-Osés
authors.forename: Carlos
authors.initials: C
authors.lastname: Aydillo
authors.forename: Jesús H
authors.initials: JH
authors.lastname: Busto
authors.forename: María M
authors.initials: MM
authors.lastname: Zurbano
authors.forename: Jesús M
authors.initials: JM
authors.lastname: Peregrina
authors.forename: Alberto
authors.initials: A
authors.lastname: Avenoza
mesh_terms: D000478:Alkylation; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001593:Benzyl Compounds; C521837:alpha-benzylserine; D012694:Serine