Synfacts 2008(4): 0415-0415  
DOI: 10.1055/s-2008-1042825
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Addition of Ketones and Nitriles to 1,3-Dienes Promoted by t-BuOK

Contributor(s): Paul Knochel, Andrei Gavryushin
J.-M. Gaudin*, P. Millet
Firmenich SA, Geneva, Switzerland
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19. März 2008 (online)


The addition of C-H compounds to 1,3-dienes has been known for many years, however, it normally required a transition-metal catalyst; besides, the pK a value of the nucleophile should be relatively low. Herein, a very simple and elegant protocol for the addition of simple ketones and nitriles to 1,3-dienes is described. It allows a convenient formation of relatively complex carbon frameworks by a cheap and atom-economical way. Many products prepared by this method are useful fragrances of industrial interest.