N-Heterocyclic Carbene Catalyzed Quadruple Domino Reactions through α,β-Unsaturated Acyl Azolium Intermediates : Asymmetric Synthesis of Cyclopenta[c]chromenones
Liu, Q., Chen, X.-Y., Puttreddy, R., Rissanen, K., & Enders, D. (2018). N-Heterocyclic Carbene Catalyzed Quadruple Domino Reactions through α,β-Unsaturated Acyl Azolium Intermediates : Asymmetric Synthesis of Cyclopenta[c]chromenones. Angewandte Chemie, 57(52), 17100-17103. https://doi.org/10.1002/anie.201810402
Published inAngewandte Chemie
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
An N‐heterocyclic carbene catalyzed domino sequence via α,β‐unsaturated acyl azolium intermediates has been developed. This strategy provides a convenient enantioselective route to functionalized tricyclic coumarin derivatives and cyclopentanes. DFT studies and control experiments were performed to gain better insight into the reaction mechanism.
PublisherWiley, VCH Verlag GmbH & Co. KGaA
Publication in research information system
MetadataShow full item record
Showing items with similar title or keywords.
N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Pentacyclic Spirooxindoles via [3+3] Annulations of Isatin-Derived Enals and Cyclic N-Sulfonyl Ketimines Liu, Qiang; Chen, Xiangyu; Li, Sun; Rissanen, Kari; Enders, Dieter (Wiley - VCH Verlag GmbH & Co. KGaA, 2019)A convenient enantioselective route to new types of pentacyclic spirooxindoles via [3+3] annulation reactions of isatin-derived enals and cyclic N-sulfonyl ketimines, using N-heterocyclic carbene (NHC) catalysis has ...
Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives Chen, Xiang-Yu; Xiong, Jia-Wen; Liu, Qiang; Li, Sun; Sheng, He; von Essen, Carolina; Rissanen, Kari; Enders, Dieter (Wiley-VCH., 2018)A strategy to control the switch between a non‐cycloaddition reaction and a cycloaddition reaction of enals, using N‐heterocyclic carbene (NHC) catalyisis, has been developed. The new scalable protocol leads to γ‐amino‐acid ...
Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis : An Efficient Asymmetric Route to Cyclohexenes Chen, Xiang-Yu; Li, Sun; Liu, Qiang; Kumar, Mukesh; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter (Wiley, 2018)Ahighly efficient strategy for the kinetic resolu-tion of Michael adductswas realized using achiral N-het-erocyclic carbene catalyst.The kinetic resolution providesanew convenientroute to single diastereomers of cyclo-hexenes ...
Zhang, Jingyu; Xia, Wei; Qu, Meilin; Huda, Saskia; Ward, Jas; Rissanen, Kari; Albrecht, Markus (Wiley-VCH Verlag, 2021)Subsequent reduction and dearomatizing cyclization reactions open up an entry into the synthesis of novel N-fused polycyclic indolines. The dearomatizing cyclization as key step of the sequence proceeds well with Cu(OTf)2 ...
Preparation and Characterization of P2BCh Ring Systems (Ch=S, Se) and Their Reactivity with N-Heterocyclic Carbenes Graham, Cameron M. E.; Millet, Clément R. P.; Price, Amy N.; Valjus, Juuso; Cowley, Michael J.; Tuononen, Heikki; Ragogna, Paul J. (Wiley-VCH., 2018)Four-membered rings with a P2BCh core (Ch = S, Se) have been synthesized via reaction of phosphinidene chalcogenide (Ar*P=Ch) and phosphaborene (Mes*P=BNR2). The mechanistic pathways towards these rings are explained ...