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The Vinylogous aldol and related addition reactions: ten years of progress

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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DOI: 10.1021/cr100304n

Abstract

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.

Item Type:Article
ID Code:6883
Status:Published
Refereed:Yes
Uncontrolled Keywords:Vinylogous aldol, Mannich process, Michael reactions
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:American Chemical Society
eISSN:1520-6890
Deposited On:19 Dec 2011 10:19

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