An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.
Functionalized azabicycloalkane amino acids by nitrone 1,3-dipolar intramolecular cycloaddition / L. Manzoni, D. Arosio, L. Belvisi, A. Bracci, M. Colombo, D. Invernizzi, C. Scolastico. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 70:10(2005), pp. 4124-4132.
Functionalized azabicycloalkane amino acids by nitrone 1,3-dipolar intramolecular cycloaddition
D. ArosioSecondo
;L. Belvisi;A. Bracci;D. InvernizziPenultimo
;C. ScolasticoUltimo
2005
Abstract
An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.
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