The gold-catalyzed oxidation of N-tosyl-protected 6-alkynyl-3,4-dihydro-2H-pyridines was studied in detail to obtain divinyl ketones in which one of the double bonds is embedded in a heterocyclic framework. The best reaction conditions were then extended to different types of substrates to assess the scope of the reaction. DFT calculations were exploited to gain insight into the regio- and chemoselectivity of the process too. The obtained divinyl ketones were then easily cyclized by a Nazarov process and the bi- or polycyclic compounds used as scaffolds in the synthesis of analogues of the plant hormones strigolactones.

A Gold(I)-Catalyzed Oxidative Rearrangement of Heterocycle-Derived 1,3-Enynes Provides an Efficient and Selective Route to Divinyl Ketones / Stefano, Nejrotti; Gabriele Prina Cerai, ; Alberto, Oppedisano; Andrea, Maranzana; Occhiato, ERNESTO GIOVANNI; Scarpi, Dina; Annamaria, Deagostino; Cristina, Prandi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2017), pp. 6228-6238. [10.1002/ejoc.201701212]

A Gold(I)-Catalyzed Oxidative Rearrangement of Heterocycle-Derived 1,3-Enynes Provides an Efficient and Selective Route to Divinyl Ketones

Ernesto G. Occhiato;Dina Scarpi;
2017

Abstract

The gold-catalyzed oxidation of N-tosyl-protected 6-alkynyl-3,4-dihydro-2H-pyridines was studied in detail to obtain divinyl ketones in which one of the double bonds is embedded in a heterocyclic framework. The best reaction conditions were then extended to different types of substrates to assess the scope of the reaction. DFT calculations were exploited to gain insight into the regio- and chemoselectivity of the process too. The obtained divinyl ketones were then easily cyclized by a Nazarov process and the bi- or polycyclic compounds used as scaffolds in the synthesis of analogues of the plant hormones strigolactones.
2017
6228
6238
Stefano, Nejrotti; Gabriele Prina Cerai, ; Alberto, Oppedisano; Andrea, Maranzana; Occhiato, ERNESTO GIOVANNI; Scarpi, Dina; Annamaria, Deagostino; Cristina, Prandi
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1106396
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