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Synlett 1999; 1999(12): 1951-1953
DOI: 10.1055/s-1999-2974
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DBU-MeOH Promoted One-Pot Stereoselective γ-Functionalization of 1,3-Dicarbonyls: Reactivity of β-Ketoamides Towards α,β-Unsaturated Aldehydes

Emmanuelle Charonnet* , Marie-Hélène Filippini, Jean Rodriguez
  • *Laboratoire RéSo, Réactivité en Synthèse Organique, UMR au CNRS 6516, Centre de St Jérôme, boîte D12, 13397 Marseille cedex 20, France; E-mail: Jean.Rodriguez@reso.u-3mrs.fr
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Publication History

Publication Date:
31 December 1999 (online)

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Cyclic β-ketoamides undergo a regioselective 1,2-addition to α,β-unsaturated aldehydes leading to synthetically valuable cycloalkenones by a stereoselective one-pot γ-allylidenation promoted by DBU in MeOH.

β-ketoamides - α,β-unsaturated aldehydes - γ-aldol-dehydration sequence - γ-allylidenation

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