title: Synthesis of type II beta-turn surrogate dipeptides based on syn-alpha-amino-alpha,beta-dialkyl-beta-lactams.
abstract: The achiral bis(trimethylsilyl)methyl group acts as an efficient stereochemical determinant of the alpha-alkylation reaction in beta-branched alpha-phenyloxazolidinyl- or alpha-diphenyloxazolidinyl-beta-lactams and provides the first stereocontrolled access to syn-alpha-amino-alpha,beta-dialkyl(aryl)-beta-lactams. These products are readily transformed into type II beta-turn mimetic surrogates 2B. [reaction: see text]
authors.affiliation: Departamento de Química Organica-I, Universidad del Pais Vasco, Facultad de Quimica, Apdo 1072, 20080 San Sebastian, Spain. qppaiipj@sc.ehu.es
authors.forename: Claudio
authors.initials: C
authors.lastname: Palomo
authors.forename: Jesus M
authors.initials: JM
authors.lastname: Aizpurua
authors.forename: Iñaki
authors.initials: I
authors.lastname: Ganboa
authors.forename: Ana
authors.initials: A
authors.lastname: Benito
authors.forename: Lourdes
authors.initials: L
authors.lastname: Cuerdo
authors.forename: Raluca M
authors.initials: RM
authors.lastname: Fratila
authors.forename: Azucena
authors.initials: A
authors.lastname: Jimenez
authors.forename: Iraida
authors.initials: I
authors.lastname: Loinaz
authors.forename: José I
authors.initials: JI
authors.lastname: Miranda
authors.forename: Kinga R
authors.initials: KR
authors.lastname: Pytlewska
authors.forename: Andreea
authors.initials: A
authors.lastname: Micle
authors.forename: Anthony
authors.initials: A
authors.lastname: Linden
mesh_terms: D000478:Alkylation; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D017433:Protein Structure, Secondary; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004151:Dipeptides; D047090:beta-Lactams