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46.1.1.3.2 Variation 2: Sequential Diene Formation

DOI: 10.1055/sos-SD-046-00002

Abell, A. D.; Edmonds, M. K.Science of Synthesis, (20094635.

Ylides that contain a formyl substituent will react with an aldehyde or ketone to produce a 1,3-enal or 1,3-enone (e.g., 31) (Scheme 21). The addition of a second ylide to the 1,3-enal or 1,3-enone in situ can result in a second Wittig reaction to give a 1,3-diene. Thus, sequential addition of 2 equivalents of (triphenylphosphoranylidene)acetaldehyde to aldehyde 30 gives the corresponding E,E-dienal 32 (Scheme 21).[‌30‌]

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