Article Dans Une Revue Chirality Année : 2009

Rearrangement of β-amino alcohols and application to the synthesis of biologically active compounds

Résumé

Beta-Amino alcohols derived from natural amino acids have been used extensively as a powerful source of chirality. Transformation of the hydroxy group of these beta-amino alcohols into a good leaving group, by using trifluoroacetic anhydride, led to rearranged beta-amino alcohols in good yields and with high enantiomeric excesses. This rearrangement has allowed the transformation of substituted prolinols to substituted 3-hydroxypiperidines and linear beta-amino alcohols, issued from natural amino acids, to rearranged beta-amino alcohols.

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hal-03228895 , version 1 (31-05-2021)

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Janine Cossy, Domingo Gomez Pardo, Cécile Dumas, Olivier Mirguet, Ingrid Déchamps, et al.. Rearrangement of β-amino alcohols and application to the synthesis of biologically active compounds. Chirality, 2009, Proceedings from the 20th International Symposium on Chirality, Geneva, Switzerland, 2008, 21 (9), pp.850 - 856. ⟨10.1002/chir.20716⟩. ⟨hal-03228895⟩
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