Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition

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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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2005-05, Vol.70 (10), p.4124-4132
Hauptverfasser:	Manzoni, Leonardo, Arosio, Daniela, Belvisi, Laura, Bracci, Antonio, Colombo, Matteo, Invernizzi, Donatella, Scolastico, Carlo
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkanes - chemical synthesis Alkanes - chemistry Alkanes - metabolism Amino Acids - chemical synthesis Amino Acids - chemistry Amino Acids - metabolism Aza Compounds - chemical synthesis Aza Compounds - chemistry Aza Compounds - metabolism Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Bridged Bicyclo Compounds, Heterocyclic - metabolism Chemistry Cross-Linking Reagents - chemistry Cyclization Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Molecular Mimicry Nitrogen Oxides - chemistry Organic chemistry Preparations and properties Stereoisomerism
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo0500683