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DOI: 10.1055/sos-SD-008-00587

Venturello, P.; Barbero, M.Science of Synthesis, (20068892.

The reductive decyanation with sodium metal in liquid ammonia has been used in the stereoselective synthesis of syn-1,3-diol acetonides 36, which are important intermediates in the synthesis of alternating polyol chains, starting from the corresponding cyanohydrin acetonides 35 (Scheme 17).[‌46‌] The decyanation reaction has been carried out on α-amino nitriles in the asymmetric synthesis of optically active alkaloids using sodium metal in liquid ammonia/tetrahydrofuran.[‌47‌] The selectivity of the reaction allows the decyanation step in the presence of an N-benzyl type CN bond (e.g., 38 from 37).

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