Studies on the selective reduction of the amide link of acyclic and macrocyclic amidoketals. Unexpected cleavage and trans -acetalization with Red-Al®

Radouane Affani (1) , Denise Dugat (1)

1 SEESIB - Synthèse et étude de systèmes à intêret biologique

Selective reduction of the amide moiety of acyclic and macrocyclic amidoketals was studied in presence of various reagents (BH3 · Me2S, iBuAlH2, Red-Al®, LiAlH4). The best results were obtained with lithium aluminium hydride in the presence of triethylamine traces, whereas borane dimethyl sulfide gave rise to a partial ketal reduction of the acyclic compound and Red-Al® to a cleavage of the macrocyclic molecule accompanied by an unexpected trans-acetalization.

Mots clés: acyclic and macrocyclic amido and aminoketals; selective reduction; trans-acetalization

Domaines: Chimie organique

Radouane Affani, Denise Dugat. Studies on the selective reduction of the amide link of acyclic and macrocyclic amidoketals. Unexpected cleavage and trans -acetalization with Red-Al®. Synthetic Communications, 2007, 37, pp.3729-3740. ⟨hal-00182557⟩