Functionalized azabicycloalkane amino acids by nitrone 1,3-dipolar intramolecular cycloaddition.
[reaction: see text] 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.
Manzoni
Leonardo
L
C.N.R.-Istituto di Scienze e Tecnologie Molecolari, and Centro Interdisciplinare Studi bio-molecolari e applicazioni Industriali, Via Venezian 21, I-20133, Milano, Italy. leonardo.manzoni@istm.cnr.it
Arosio
Daniela
D
Belvisi
Laura
L
Bracci
Antonio
A
Colombo
Matteo
M
Invernizzi
Donatella
D
Scolastico
Carlo
C
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D003432:Cross-Linking Reagents / Q000737:chemistry; D003500:Cyclization; D018716:Molecular Mimicry; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism
D000473:Alkanes; D000596:Amino Acids; D001372:Aza Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003432:Cross-Linking Reagents; D009589:Nitrogen Oxides; C015388:nitrones