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20.2.11.1.3.3 Variation 3: Wittig Reaction

DOI: 10.1055/sos-SD-020-00532

Vanderwal, C. D.; Jacobsen, E. N.Science of Synthesis, (200720560.

There are several reported examples of the Wittig homologation of aldehydes to the corresponding alk-2-enoic acids using the reagent (triphenylphosphoranylidene) acetic acid 42 (Scheme 11).[‌33‌,‌34‌] Unfortunately, despite the fact that this represents a direct and attractive synthesis of the alk-2-enoic acid functionality, detailed experimental procedures including accurate yield determinations are lacking in the literature. The trimethylsilyl ester variant of this reagent (43) has also been described for the formation of the corresponding silyl alkenoate.[‌35‌] It is anticipated that the combination of this reaction with a simple aqueous acidic workup (to effect silyl ester cleavage) should afford the desired carboxylic acid in high yield, though this sequence has not been described.

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