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Phosphine-Catalyzed [3+2] Annulation of Hepta-2,3,5-trienedioates with Alkenes for the Construction of Exocyclic Olefinic Cyclopentenes.
J Org Chem
July 2023
School of Chemistry and Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Jiaotong University, Xi'an 710049, P. R. China.
Hepta-2,3,5-trienedioates have been employed as substrates to explore Lewis base-catalyzed annulation reactions. This leads to the discovery of a phosphine-catalyzed [3+2] annulation of with electron-deficient alkenes for the construction of exocyclic olefinic cyclopentenes in good yields and moderate : ratios under mild conditions. The annulation is believed to proceed in a tandem [3+2] cyclization and double bond migration in which the ε-ester is crucial to both processes.
View Article and Find Full Text PDFPhosphine-Catalyzed Activation of Alkylidenecyclopropanes: Rearrangement to Form Polysubstituted Furans and Dienones.
Angew Chem Int Ed Engl
July 2019
Department of Chemistry, School of Science and Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University, Xi'an, 710049, P. R. China.
We report a phosphine-catalyzed ring opening of electron-deficient alkylidenecyclopropanes (ACPs) to generate allylic phosphonium zwitterions that resemble the well-studied phosphine-allene adducts but exhibit distinct properties. The potent reactivity of these intermediates has been demonstrated in three types of substrate-controlled phosphine-catalyzed rearrangements of alkylidenecyclopropylketones, which chemoselectively afford tri- and tetrasubstituted furans, and trisubstituted dienones in good yields.
View Article and Find Full Text PDFSubstrate-controlled, phosphine-catalyzed domino reactions of activated conjugated dienes: highly diastereoselective synthesis of bicyclic skeletons.
Chemistry
June 2011
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University Tianjin 300071, PR China.
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