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Activation of 1,2- and 1,3-Ketoamides with Thiourea Organocatalyst for the Enantioselective Domino Synthesis of Fuctionalized Cyclohexanes

Abstract : Several reactive sites of 1,2- and 1,3-ketoamides were successively exploited in two complementary domino transformations for the synthesis of polysubstituted monocyclic or bridged bicyclic cyclohexanes, with the creation of up to six stereogenic centers. In both cases, a chiral bifunctional thiourea organocatalyst allowed efficient control of chirality in the final carbocycle.
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https://hal.archives-ouvertes.fr/hal-00861637
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Submitted on : Monday, September 16, 2013 - 2:42:52 PM
Last modification on : Tuesday, December 14, 2021 - 8:36:12 AM
Long-term archiving on: : Friday, December 20, 2013 - 1:31:13 PM

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Wilfried Raimondi, Maria del Mar Sanchez Duque, Sébastien Goudedranche, Adrien Quintard, Thierry Constantieux, et al.. Activation of 1,2- and 1,3-Ketoamides with Thiourea Organocatalyst for the Enantioselective Domino Synthesis of Fuctionalized Cyclohexanes. SYNTHESIS, Georg Thieme Verlag, 2013, 45, pp.1659-1666. ⟨10.1055/s-0033-1338844⟩. ⟨hal-00861637⟩

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