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Synlett 1999; 1999(5): 505-518
DOI: 10.1055/s-1999-2654
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Our Recent Contribution to the Field of Anionic Domino Transformations

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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This personal account presents our recent contributions to the field of anionic domino transformations involving combinations of nonidentical reactions. Our choice was to study the feasibility of processes initiated in the presence of very simple and user friendly bases such as potassium carbonate (K2CO3) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), involved in simple and well-known tranformations such as dehydrohalogenation, isomerization, Michael addition, aldolization, nucleophilic substitution, and retro-Dieckmann reaction. Sequential combinations of these different reactions have led to the proposal of new stereoselective one-pot methodologies, including up to five different steps, allowing the facile and efficient preparation of a variety of powerful synthetic intermediates such as epoxides, cis-1,2-diols, acylfurans, bridged bicyclic compounds, functionalized seven- and eight-membered rings, arylidenecycloalkanones, and substituted vinyl-, allenyl- or methylenetetrahydrofurans and pyrrolidines.

anionic domino reactions - dehydrohalogenation - isomerization - Michael addition - aldolization - nucleophilic substitution - retro-Dieckmann reaction

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