Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds

Abstract : A rhodium‐catalyzed asymmetric synthesis of 5,5‐disubstituted cyclohexa‐1,3‐dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita–Baylis–Hillman (M‐B‐H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84–97%) through a kinetic resolution of the M‐B‐H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels–Alder cycloadducts in good yields.
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Submitted on : Thursday, October 4, 2018 - 5:50:04 PM
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Martí Fernández, Magda Parera, Teodor Parella, Agustí Lledó, Jean Le Bras, et al.. Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2016, 358 (11), pp.1848 - 1853. ⟨10.1002/adsc.201600039⟩. ⟨hal-01888169⟩

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