Synthesis of type II beta-turn surrogate dipeptides based on syn-alpha-amino-alpha,beta-dialkyl-beta-lactams.
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]
Palomo
Claudio
C
Departamento de Química Organica-I, Universidad del Pais Vasco, Facultad de Quimica, Apdo 1072, 20080 San Sebastian, Spain. qppaiipj@sc.ehu.es
Aizpurua
Jesus M
JM
Ganboa
Iñaki
I
Benito
Ana
A
Cuerdo
Lourdes
L
Fratila
Raluca M
RM
Jimenez
Azucena
A
Loinaz
Iraida
I
Miranda
José I
JI
Pytlewska
Kinga R
KR
Micle
Andreea
A
Linden
Anthony
A
D000478:Alkylation; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D017433:Protein Structure, Secondary; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D004151:Dipeptides; D047090:beta-Lactams