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Synthesis of Sulfur-Containing Exo -Bicyclic Dienes and Their Diels-Alder Reactions to Access Thiacycle-Fused Polycyclic Systems

Abstract : The stereocontrolled synthesis of unprecedented sulfur-containing exo-bicyclic 1,3-dienes is reported through a palladium-catalyzed reductive cyclization of sulfur-linked 2-bromoenynes. The fused bicyclic structure provides a better stability to the thiacyclic diene compared to the simple 3,4-dimethylenetetrahydrothiophene. Their reactivity toward several dienophiles has been investigated, and various original thiacycle-fused polycyclic systems have been obtained with high or total diastereoselectivity. Moreover, they are the first exo-bicyclic dienes used in Diels–Alder reactions. The relative configurations of four cycloadducts have been unambiguously assigned by X-ray crystallographic analysis. Mechanistic details of the cycloadditions have been examined by computational means.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024483
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 19, 2019 - 11:09:06 AM
Last modification on : Thursday, July 2, 2020 - 3:28:45 AM

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T. Castanheiro, A. Schoenfelder, M. Donnard, Isabelle Chataigner, M. Gulea. Synthesis of Sulfur-Containing Exo -Bicyclic Dienes and Their Diels-Alder Reactions to Access Thiacycle-Fused Polycyclic Systems. Journal of Organic Chemistry, American Chemical Society, 2018, 83 (8), pp.4505-4515. ⟨10.1021/acs.joc.8b00213⟩. ⟨hal-02024483⟩

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