From a remarkable manifestation of polar effects in a radical fragmentation to the convergent synthesis of highly functionalized ketones.

Laurent Debien; Samir Z Zard

doi:10.1021/ja400831w

From a remarkable manifestation of polar effects in a radical fragmentation to the convergent synthesis of highly functionalized ketones.

Laurent Debien ¹ Samir Z Zard ¹

1 DCSO - Laboratoire de synthèse organique

Abstract : A new radical addition/C-C bond fragmentation process is reported. Vinyl carbinols derived from 2-methyl-2-phenylpropanal react with radicals generated from xanthates to give the corresponding ketones. The radical cleavage reaction proceeds under mild conditions, in good to high yield, and in the presence of the unprotected carbinol. Highly functionalized 1,5-diketones and pyridines are readily available using this approach.

Type de document :

Article dans une revue

Journal of the American Chemical Society, American Chemical Society, 2013, 135 (10), pp.3808-3811. 〈10.1021/ja400831w〉

Domaine :

Chimie / Chimie organique

Liste complète des métadonnées

https://hal-polytechnique.archives-ouvertes.fr/hal-00966618
Contributeur : Denis Roura <>
Soumis le : mercredi 26 mars 2014 - 21:53:34
Dernière modification le : jeudi 10 mai 2018 - 02:07:27

From a remarkable manifestation of polar effects in a radical fragmentation to the convergent synthesis of highly functionalized ketones.

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From a remarkable manifestation of polar effects in a radical fragmentation to the convergent synthesis of highly functionalized ketones.

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