Asymmetric Synthesis of Spirocyclic β‐Lactams via Copper‐Catalyzed Kinugasa/Michael Domino Reactions
Shu, T., Zhao, L., Li, S., Chen, X.-Y., von Essen, C., Rissanen, K., & Enders, D. (2018). Asymmetric Synthesis of Spirocyclic β‐Lactams via Copper‐Catalyzed Kinugasa/Michael Domino Reactions. Angewandte Chemie, 130(34), 11151-11154. https://doi.org/10.1002/ange.201806931
Published inAngewandte Chemie
Shu, Tao |
Li, Sun |
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA
The first copper‐catalyzed highly chemo‐, regio‐, diastereo‐, and enantioselective Kinugasa/Michael domino reaction for the desymmetrization of prochiral cyclohexadienones is described. In the presence of a chiral copper catalyst, alkyne‐tethered cyclohexadienones couple with nitrones to generate the chiral spirocyclic lactams with excellent stereoselectivity (up to 97 % ee, >20:1 dr). The new method provides direct access to versatile highly functionalized spirocyclic β‐lactams possessing four contiguous stereocenters, including one quaternary and one tetra‐substituted stereocenter.
Publication in research information system
MetadataShow full item record
Showing items with similar title or keywords.
Organocatalytic Oxa-Michael/Michael/Michael/Aldol Condensation Quadruple Domino Sequence : Asymmetric Synthesis of Tricyclic Chromanes Kumar, Mukesh; Chauhan, Pankaj; Bailey, Stephen J.; Jafari, Ehsan; von Essen, Carolina; Rissanen, Kari; Enders, Dieter (American Chemical Society, 2018)An efficient and highly stereoselective one-pot, four-component synthesis of functionalized tricyclic chromanes has been achieved through an organocatalyzed quadruple domino reaction. The reaction sequence involves an ...
N-Heterocyclic Carbene Catalyzed Quadruple Domino Reactions through α,β-Unsaturated Acyl Azolium Intermediates : Asymmetric Synthesis of Cyclopenta[c]chromenones Liu, Qiang; Chen, Xiang-Yu; Puttreddy, Rakesh; Rissanen, Kari; Enders, Dieter (Wiley, VCH Verlag GmbH & Co. KGaA, 2018)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 ...
Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol Fekete, Beáta; Palkó, Márta; Haukka, Matti; Fülöp, Ferenc (MDPI, 2017)From 2-aminonorbornene hydroxamic acids, a simple and efficient method for the preparation of pyrrolo[1,2-a]pyrimidine enantiomers is reported. The synthesis is based on domino ring-closure followed by microwave-induced ...
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 ...
Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution Axelsson, Anton; Westerlund, Mathias; Zacharias, Savannah C.; Runemark, August; Haukka, Matti; Sundén, Henrik (Wiley, 2021)An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, ...