Preparation of non-racemic single-stereocentre a-aminonitriles and a study of their fate in Bruylants reactions. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2006

Preparation of non-racemic single-stereocentre a-aminonitriles and a study of their fate in Bruylants reactions.

Résumé

A number of chiral carboxamide dehydration methods were investigated for the preparation of four representative enantiomerically enriched α-aminonitriles possessing only one stereogenic centre; best results were observed using Burgess' salt (yield up to 87%, er up to 92/8) or the trifluoroacetic anhydride–triethylamine combination (yield up to 98%, er up to 86/14). Two of the aminonitriles thus obtained were subjected to Bruylants reactions with a methyl Grignard reagent to furnish the corresponding tertiary amines; these products, along with any unreacted starting materials, were obtained essentially in racemic form. In accord with the accepted mechanism for this reaction, a magnesium species is implicated in the formation of an iminium, the common intermediate for both chemical transformation and racemization processes.

Domaines

Chimie organique
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Dates et versions

hal-00118398 , version 1 (16-02-2007)

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Virginie Beaufort-Droal, Elisabeth Pereira, Vincent Thery, David J Aitken. Preparation of non-racemic single-stereocentre a-aminonitriles and a study of their fate in Bruylants reactions.. Tetrahedron, 2006, 62, pp.11948-11954. ⟨10.1016/j.tet.2006.09.087⟩. ⟨hal-00118398⟩
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