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The MARDi cascade : A Michael-Initiated Domino-Multicomponent Approach for the Stereoselective Synthesis of Seven-Membered Rings

Yoann Coquerel 1, * Marie-Hélène Filippini 1 David Bensa 1 Jean Rodriguez 1, * 
* Corresponding author
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : The MARDi cascade is a recently invented three-component condensation involving 1,3-dicarbonyl derivatives. It allows the regio- and stereocontrolled access to a variety of functionalized and substituted seven-membered rings. The substitution array can be diastereoselectively modulated by appropriate choice of the reaction partners, and the reaction allows the control of up to five newly created stereocenters and a complete chiral induction in the case of an optically active ketone precursor. The high level of diastereoselectivity observed has been attributed to a total thermodynamical control of the reaction. The attractiveness of the present domino three-component approach to seven-membered rings resides in the diversity of carbo- and heterocyclic structures that can be accessed with total regiocontrol and high stereocontrol starting from simple substrates, under user and environmentally friendly conditions, as now required in modern organic chemistry.
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https://hal.archives-ouvertes.fr/hal-00680586
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Submitted on : Monday, March 19, 2012 - 5:03:44 PM
Last modification on : Tuesday, December 14, 2021 - 8:36:12 AM

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Yoann Coquerel, Marie-Hélène Filippini, David Bensa, Jean Rodriguez. The MARDi cascade : A Michael-Initiated Domino-Multicomponent Approach for the Stereoselective Synthesis of Seven-Membered Rings. Chemistry - A European Journal, Wiley-VCH Verlag, 2008, 14, pp.3078-3092. ⟨10.1002/chem.200701708⟩. ⟨hal-00680586⟩

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