Literature DB >> 29446638

Chiral-at-Metal Rh(III) Complex-Catalyzed Michael Addition of Pyrazolones with α,β-Unsaturated 2-Acyl Imidazoles.

Shi-Wu Li1,2, Qian Wan1, Qiang Kang1.   

Abstract

An efficient enantioselective conjugate addition of pyrazolones with α,β-unsaturated 2-acyl imidazoles catalyzed by chiral-at-metal rhodium complex is reported. The corresponding adducts were obtained in good yields (85%-96%) with excellent enantioselectivities (up to >99%). This protocol exhibits extraordinary reactivity, because of the fact that a complex with as little as 0.05 mol % Rh(III) can catalyze the title reaction on a gram-scale with excellent enantioselectivity.

Entities:  

Year:  2018        PMID: 29446638     DOI: 10.1021/acs.orglett.8b00040

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement to construct homoallyl sulfur-containing pyrazolones.

Authors:  Shou-Jie Shen; Xiao-Li Du; Xiao-Li Xu; Yue-Hua Wu; Ming-Gang Zhao; Jin-Yan Liang
Journal:  RSC Adv       Date:  2019-10-29       Impact factor: 4.036

2.  Stretchable chiral pockets for palladium-catalyzed highly chemo- and enantioselective allenylation.

Authors:  Yuchen Zhang; Xue Zhang; Shengming Ma
Journal:  Nat Commun       Date:  2021-04-23       Impact factor: 14.919

3.  Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones.

Authors:  Amy Boylan; Thien S Nguyen; Brian J Lundy; Jian-Yuan Li; Ravikrishna Vallakati; Sasha Sundstrom; Jeremy A May
Journal:  Molecules       Date:  2021-03-14       Impact factor: 4.411

4.  Synthesis of 1-(β-coumarinyl)-1-(β-indolyl)trifluoroethanols through regioselective Friedel-Crafts alkylation of indoles with β-(trifluoroacetyl)coumarins catalyzed by Sc(OTf)3.

Authors:  Lijun Shi; Ying Liu; Caixia Wang; Xinxin Yuan; Xiaobiao Liu; Lulu Wu; Zhenliang Pan; Qicheng Yu; Cuilian Xu; Guoyu Yang
Journal:  RSC Adv       Date:  2020-04-15       Impact factor: 4.036

5.  Bis-Cyclometalated Indazole Chiral-at-Rhodium Catalyst for Asymmetric Photoredox Cyanoalkylations.

Authors:  Philipp S Steinlandt; Wei Zuo; Klaus Harms; Eric Meggers
Journal:  Chemistry       Date:  2019-11-13       Impact factor: 5.236

  5 in total

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