Science of Synthesis

Venturello, P.; Barbero, M., Science of Synthesis, (2006) 8, 892.

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 C—N bond (e.g., ‌38‌ from ‌37‌).

‌Meeeee 88‌ Meeeeeeee Meeeeeee ee Meeeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

α-Meeee eeeeeee ‌88‌ (8.8 eeee) ee MMM (8 eM) eee eeeee ee e eeee eeee eeee ee Me (8 eeee) ee eee MM8 (88 eM) ee −88°M, eee eee eeeeeee eee eeeeeee ee eeeee eee 88 eee. Meeee eeeee eeeeee, eee eeeeeeeeee eeeeeee eee eeeeeeee ee eeeeeeeee eeeee. Mee eeeeeee eee eeeeee eeee Me8M ee e eeeeee eeeeeeee ee eee, eee eeee eeeeeeeeee eeee M8M. Mee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee (Me8M). Mee Me8M eeeeeeee eeee eeeeeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeee ee eeee eee eeeeeeeeee eeeeeeee ee eeeeeeeee eeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.