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Article Dans Une Revue Tetrahedron Letters Année : 2004

Liquid and solide phase syntheses of orthogonally protected α-hydrazinoacid derivatives

Résumé

The first solid phase synthesis of chiral α-hydrazinoacids has been developed. This synthesis was achieved by the preparation of solid supported-N-alkyloxycarbonyl-aminophthalimides used as acidic partners in the Mitsunobu protocol involving α-hydroxyesters. Two different final trans-protection steps of the phthaloyl group, developed first in liquid phase, result in efficient releases of orthogonally bis-protected or fully tris-protected hydrazine derivatives. A comparison between liquid and solid phase syntheses is outlined: even if the overall yields are sometimes rather higher by the liquid phase synthesis, the on-resin protocol is much more rapid and convenient than the liquid protocol

Dates et versions

hal-00097374 , version 1 (21-09-2006)

Identifiants

Citer

Isabelle Bouillon, Nicolas Brosse, Régis Vanderesse, Brigitte Jamart-Grégoire. Liquid and solide phase syntheses of orthogonally protected α-hydrazinoacid derivatives. Tetrahedron Letters, 2004, 45 (18), pp.3569-3572. ⟨10.1016/j.tetlet.2004.03.063⟩. ⟨hal-00097374⟩
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