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Synthesis 2017; 49(11): 2297-2336
DOI: 10.1055/s-0036-1589487
DOI: 10.1055/s-0036-1589487
review
Enolizable Alkylidene Heterocyclic and Carbocyclic Carbonyl Systems: Valuable Vinylogous Donor Substrates in Synthesis
Authors
Weitere Informationen
Publikationsverlauf
Received: 25. November 2016
Accepted after revision: 24. Januar 2017
Publikationsdatum:
06. April 2017 (online)
To the memory of Prof. Giovanni Casiraghi, our mentor, with deep gratitude (1939–2016)
Abstract
Controlled vinylogous carbon–carbon bond-forming reactions are useful options for providing the selective remote functionalization of conjugated carbonyl substrates. Remotely enolizable alkylidene heterocyclic and carbocyclic carbonyl compounds are pro-nucleophilic substrates that may be engaged in highly valuable chemical transformations. This review emphasizes the merits of these recently discovered vinylogous donors in the chemo-, regio- and stereoselective synthesis of many functionality-rich products.
1 Introduction
2 Alkylidene Oxindoles
3 Alkylidene Pyrazolinones
4 Alkylidene Furanones
5 Alkylidene Azlactones
6 Cycloalkylidene Carbonyl Compounds
7 Alkylidene Indenones
8 Cycloalkylidene Malononitriles
9 Conclusion
-
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For focused review articles on vinylogy, see:
For a couple of brilliant examples where similar ylides were generated in situ by isatin-derived MBH carbonates and used in subsequent [2+1] and [3+2] annulations; see:
For representative articles on tertiary amine/(thio)urea organocatalysts, see:
For leading articles on squaramide-embedding organocatalysts, see:
Selected examples:
Selected examples:
For other examples of vinylogous Michael additions of cycloalkylidene malononitriles to nitroolefins in the period 2005–2010, see: