Literature DB >> 26527108

Chiral Sulfinamide Bisphosphine Catalysts: Design, Synthesis, and Application in Highly Enantioselective Intermolecular Cross-Rauhut-Currier Reactions.

Wei Zhou1, Xiao Su1, Mengna Tao1, Chaoze Zhu1, Qingjie Zhao2,3, Junliang Zhang4.   

Abstract

A novel type of highly efficient chiral sulfinamide bisphosphine catalysts (Wei-Phos) were developed. These could be easily prepared from commercially available starting materials. Wei-Phos has shown good performance in the very challenging intermolecular cross-Rauhut-Currier reactions of vinyl ketones and 3-acyl acrylates or 2-ene-1,4-diones, leading to the R-C products in high yields with up to 99% ee under 2.5-5 mol% catalyst loading. The highly regio- and enantio-selective cross-Rauhut-Currier reactions of 2-ene-1,4-diones and vinyl ketone have yet reported so far.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Rauhut-Currier reaction; alkenes; asymmetric catalysis; chiral sulfinamidephosphines; organocatalysis

Year:  2015        PMID: 26527108     DOI: 10.1002/anie.201508108

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  9 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones.

Authors:  Wei Zhou; Huamin Wang; Mengna Tao; Chao-Ze Zhu; Tao-Yan Lin; Junliang Zhang
Journal:  Chem Sci       Date:  2017-04-19       Impact factor: 9.825

3.  Catalytic Enantiodivergent Michael Addition by Subtle Adjustment of Achiral Amino Moiety of Dipeptide Phosphines.

Authors:  Huamin Wang; Xiuzheng Li; Youshao Tu; Junliang Zhang
Journal:  iScience       Date:  2020-05-06

4.  Design, synthesis and application of a new type of bifunctional Le-Phos in highly enantioselective γ-addition reactions of N-centered nucleophiles to allenoates.

Authors:  Haile Qiu; Xiaofeng Chen; Junliang Zhang
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

5.  Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes.

Authors:  Mingyue Wu; Zhaobin Han; Huanzhen Ni; Nengzhong Wang; Kuiling Ding; Yixin Lu
Journal:  Chem Sci       Date:  2022-02-11       Impact factor: 9.825

6.  Synthetic Approach toward Enantiopure Cyclic Sulfinamides.

Authors:  Glebs Jersovs; Matiss Bojars; Pavel A Donets; Edgars Suna
Journal:  Org Lett       Date:  2022-06-16       Impact factor: 6.072

7.  Access to P-chiral sec- and tert-phosphine oxides enabled by Le-Phos-catalyzed asymmetric kinetic resolution.

Authors:  Haile Qiu; Qiang Dai; Jiafeng He; Wenbo Li; Junliang Zhang
Journal:  Chem Sci       Date:  2020-09-02       Impact factor: 9.825

8.  Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3-Isothiocyanato Oxindoles with Dibenzylidene Ketones.

Authors:  Dan Du; Yu Jiang; Qin Xu; Xiao-Ge Li; Min Shi
Journal:  ChemistryOpen       Date:  2016-05-25       Impact factor: 2.911

9.  Enantioselective desymmetrization of cyclohexadienones via an intramolecular Rauhut-Currier reaction of allenoates.

Authors:  Weijun Yao; Xiaowei Dou; Shan Wen; Ji'en Wu; Jagadese J Vittal; Yixin Lu
Journal:  Nat Commun       Date:  2016-10-04       Impact factor: 14.919

  9 in total

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