Synthesis of chiral primary amines: diastereoselective alkylation of N-[(1E)-alkylidene]-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amines and N4–Nexocyclic bond cleavage in the resulting 1,2,4-triazol-4-alkylamines

Albalat, Muriel; Roussel, Christian; Vanthuyne, Nicolas; Vallejos, Jean-Claude; Wilhelm, Didier

doi:10.1016/j.tetasy.2008.12.015

Tetrahedron: Asymmetry

2008

DOI: 10.1016/j.tetasy.2008.12.015

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Synthesis of chiral primary amines: diastereoselective alkylation of N-[(1E)-alkylidene]-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amines and N4–Nexocyclic bond cleavage in the resulting 1,2,4-triazol-4-alkylamines

Muriel Albalat¹,

Christian Roussel²,

Nicolas Vanthuyne³

et al.

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Cited by 3 publications

References 37 publications

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Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

Albalat¹,

Primazot²,

Wilhelm³

et al. 2011

Amino Acids

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The first successful resolution of rac-α-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of α-aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N-protection and a new efficient hydrolysis step followed by a reduction of the resulting N-protected α-aminoaldehyde intermediates. A racemization method of optically enriched α-aminoacetals is exemplified to allow valorisation of both enantiomers.

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Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

Albalat¹,

Primazot²,

Wilhelm³

et al. 2011

Amino Acids

Self Cite

View full text Add to dashboard Cite

show abstract

Cyanuric chloride: an efficient reagent for the Lossen rearrangement

Hamon

Prié

Lecornué

et al. 2009

Tetrahedron Letters

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Organocatalytic asymmetric biomimetic transamination of α-keto acetals to chiral α-amino acetals

et al. 2014

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Synthesis of chiral primary amines: diastereoselective alkylation of N-[(1E)-alkylidene]-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amines and N4–Nexocyclic bond cleavage in the resulting 1,2,4-triazol-4-alkylamines

Cited by 3 publications

References 37 publications

Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

Cyanuric chloride: an efficient reagent for the Lossen rearrangement

Organocatalytic asymmetric biomimetic transamination of α-keto acetals to chiral α-amino acetals

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