Casiraghi, Giovanni and Battistini, Lucia and Curti, Claudio and Rassu, Gloria Maria Rita and Zanardi, Franca (2011) The Vinylogous aldol and related addition reactions: ten years of progress. Chemical Reviews, Vol. 111 (5), p. 3076-3154. eISSN 1520-6890. Article.
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Rephrasing Fuson's original formulation, the principle of vinylogy explains how the influence of a functional group may be relayed to a distant point in the molecule when these two sites are connected to by conjugated unsaturated linkages, such as double and triple bonds or aromatic moieties. This principle has been applied, over the years, to the majority of polar carbon-carbon bond-forming reactions of various repute, including the venerable Michael addition reaction, where the electrophilic -CdX site (1,2-addition) is “usurped” by a remote conjugated -RCdCR-CdX position (1,4-addition). The aldol addition reaction and the related Mannich process, both fundamental pillars of organic synthesis, have not escaped this fate, and both of their vinylogous extensions have emerged as extremely valuable synthetic methodologies.
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