title: Access to alpha-substituted amino acid derivatives via 1,3-dipolar cycloaddition of alpha-amino ester derived nitrones.
abstract: 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.
authors.affiliation: UCO2M 6011 CNRS, Universite du Maine, 72085 Le Mans, France.
authors.forename: Thanh Binh
authors.initials: TB
authors.lastname: Nguyen
authors.forename: Alice
authors.initials: A
authors.lastname: Beauseigneur
authors.forename: Arnaud
authors.initials: A
authors.lastname: Martel
authors.forename: Robert
authors.initials: R
authors.lastname: Dhal
authors.forename: Mathieu
authors.initials: M
authors.lastname: Laurent
authors.forename: Gilles
authors.initials: G
authors.lastname: Dujardin
mesh_terms: 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*
chemical_list: D000475:Alkenes; D000596:Amino Acids; D004952:Esters; D009589:Nitrogen Oxides; D014753:Vinyl Compounds; C015388:nitrones; C100195:vinyl ether