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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Enantioselective Synthesis of ε-Lactams via Rh(I)-Catalyzed C─C Bond Activation
Shiyuan Sui1, Hao Wu1, Yuanyuan Guo1
1State Key Laboratory of Antiviral Drugs, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, School of Chemistry and Chemical Engineering, Pingyuan Laboratory, Henan Normal University, Xinxiang, 453007, China.
Abstract:
ε-Lactams are important structural motifs in medicinal chemistry, but a fully enantioselective synthesis without byproduct formation represents a challenge that has attracted significant research interest. Herein, we report an atom- and step-economic synthesis of chiral ε-lactams via Rh(I)-catalyzed enantioselective C─C bond activation of aminocyclopropanes. The catalytic C─C bond activation enables a directed generation of chiral rhodacyclobutanes that circumvents β-hydride decomposition. Subsequent enantioselective cycloaddition of the alkene unit and then fragmentation generates chiral ε-lactams. A range of enantioenriched ε-lactams have been obtained with excellent regio- and enantioselectivities, which can undergo several stereospecific transformations. Theoretical calculations are performed to reveal the reaction mechanism and the origin of enantioselectivity control.
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