Alpha,gamma-diamino acids: asymmetric synthesis of new constrained 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acids.
The synthesis of two new diastereomeric 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acids exo- and endo-8,9 is reported using exo- and endo-norbornene amino acids as chiral building blocks. This method provides a fast access to optically pure amino acids 8 and 9 which can be considered both alpha,gamma- and alpha,delta-diamino acids containing sterical constraints and characterized by alpha,alpha-disubstitution.
Caputo
Francesco
F
Istituto di Chimica Organica "A. Marchesini", Facoltà di Farmacia, Università di Milano, Via Venezian 21, I-20133 Milano, Italy.
Cattaneo
Cristian
C
Clerici
Francesca
F
Gelmi
Maria Luisa
ML
Pellegrino
Sara
S
D000599:Amino Acids, Diamino / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry; D013237:Stereoisomerism; D013997:Time Factors
D000599:Amino Acids, Diamino; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002264:Carboxylic Acids; D009636:Norbornanes