Access to alpha-substituted amino acid derivatives via 1,3-dipolar cycloaddition of alpha-amino ester derived nitrones.
Amino acid derived nitrones were conveniently synthesized in good-to-excellent yields by condensation of alpha-ketoesters with N-benzylhydroxylamine. The cycloaddition reactions of these nitrones with different alkenes were investigated under thermal solvent-free conditions. Considering conversions, yields, and selectivities, alkyl vinyl ethers have proven to be valuable partners to achieve this transformation, which creates a tetrafunctionalized stereogenic quaternary center. From the adducts derived from vinyl ethers, a three-step access to highly functionalized alpha-substituted amino acid derivatives is described.
Nguyen
Thanh Binh
TB
UCO2M 6011 CNRS, Universite du Maine, 72085 Le Mans, France.
Beauseigneur
Alice
A
Martel
Arnaud
A
Dhal
Robert
R
Laurent
Mathieu
M
Dujardin
Gilles
G
D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D055601:Organic Chemistry Phenomena; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014753:Vinyl Compounds / Q000737:chemistry*
D000475:Alkenes; D000596:Amino Acids; D004952:Esters; D009589:Nitrogen Oxides; D014753:Vinyl Compounds; C015388:nitrones; C100195:vinyl ether