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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Bibliographic Details
Published in:Journal of organic chemistry 2005-05, Vol.70 (10), p.4124-4132
Main Authors: Manzoni, Leonardo, Arosio, Daniela, Belvisi, Laura, Bracci, Antonio, Colombo, Matteo, Invernizzi, Donatella, Scolastico, Carlo
Format: Article
Language:English
Subjects:
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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Description
Summary: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