Domino Palladium(II)-Mediated Rearrangement-Oxidative Cyclization of β-Aminocyclopropanols

Stefano Cicchi; Julia Revuelta; Alessandra Zanobini; Matteo Betti; Alberto Brandi

doi:10.1055/s-2003-42122

LETTER

Domino Palladium(II)-Mediated Rearrangement-Oxidative Cyclization of β-Aminocyclopropanols

Stefano Cicchi, Julia Revuelta, Alessandra Zanobini, Matteo Betti, Alberto Brandi*
Dipartimento di Chimica Organica ‘Ugo Schiff’, Universita` di Firenze and Istituto di Chimica dei Composti Organo Metallici-ICCOM-CNR, Via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy
Fax: +39(055)4573572; e-Mail: alberto.brandi@unifi.it;

Abstract

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Abstract

β-Aminocyclopropanols were transformed, in a domino process catalyzed by Pd(II) salts, into the corresponding 2,3-dihydro-1H-pyridin-4-ones. Conversely the use of a Pd(0) derivative, Pd(dba)₂, afforded the corresponding tetrahydropyrid-4-ones. The saturated derivatives were also obtained, in better yields, using Pd(II) and Cu(OAc)₂ as stoichiometric oxidant.

Key words

domino reactions - palladium - Wacker reactions - heterocycles - catalysis

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References

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