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36.3.1.1.1 Variation 1: Meerwein–Ponndorf–Verley Reduction

DOI: 10.1055/sos-SD-036-00434

Forgione, P.; Fader, L. D.Science of Synthesis, (200836532.

In their investigation of electronic effects on the rates of DielsAlder reactions, Dudkowski and Becker reported one of the earliest examples of this transformation where the MeerweinPonndorfVerley reduction was applied to 3-phenylprop-2-ynal (1) to give 3-phenylprop-2-yn-1-ol (2) (Scheme 1).[‌10‌] Although the generality of this method for this substrate class is unknown, the method proved superior to Grignard addition of magnesiated phenylacetylene onto formaldehyde and other strategies known at the time.

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References