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36.3.1.1.2 Variation 2: Hydride-Type Reduction of Alkynals

DOI: 10.1055/sos-SD-036-00434

Forgione, P.; Fader, L. D.Science of Synthesis, (200836534.

A widespread method of reducing aldehydes and other carbonyl functionalities is the use of hydride-type reducing reagents. These reductants can be used for the chemoselective 1,2-reduction of alkynals (Scheme 3), although lithium aluminum hydride should be avoided due to its ability to reduce propargylic alcohols to trans-disubstituted allylic alcohols.[‌13‌] The commonly employed diisobutylaluminum hydride is suitable for this transformation, as illustrated by the reduction of oct-2-ynal (4) to give the propargylic alcohol 5.[‌14‌]

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Mee-8-ee-8-ee (8); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eee-8-eeee (8; 8.8e, 88.8eeee) ee eee MMM (888eM) eee eeeeee ee 88°M. 8.8M MMMMM-M ee eeeeeee (88.8eM, 88.8eeee) eee eeeee eeeeeeee eee eee eeeeeee eee eeeeeee eee 8e. M eee. eeee ee Meeeeeee'e eeee eee eeeeeeeee eeeee, eeeeeeee ee eeeeeeee (8.8eM eee eeee ee MMMMM-M) eee eee eeeeeeee eeeeee eee eeeeeee ee ee eee 8e. Mee eeeeeee eee eeeeeeeee eeee MeMMe (8×), eee eee eeeeeeee eeeeeee eeeee eee eeeeee eeee eeeee eee eeeee (Me8MM8). Meeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeee/MeMMe) eeee eeeeeee 8; eeeee: 8.88e (88%); 8M MMM (MMMe8, δ): 8.8 (e, M=8.8Me, 8M), 8.8 (e, M=8.8Me, 8M), 8.8 (ee e, 8M), 8.8 (e, M=8.8Me, 8M), 8.88.8 (ee e, 8M), 8.8 (e, M=8.8Me, 8M); 88M MMM (MMMe8, δ): 88.8, 88.8, 88.8, 88.8, 88.8, 88.8, 88.8, 88.8.

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