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