Literature DB >> 25753678

Phosphahelicenes in asymmetric organocatalysis: [3+2] cyclizations of γ-substituted allenes and electron-poor olefins.

Maxime Gicquel1, Yang Zhang, Paul Aillard, Pascal Retailleau, Arnaud Voituriez, Angela Marinetti.   

Abstract

The first use of phosphahelicene in enantioselective organocatalysis is reported. New chiral phosphahelicenes have been prepared and enable highly enantioselective [3+2] cyclization reactions between arylidene- or alkylidenemalononitriles and γ-substituted allenoates or cyanoallenes. These reactions afford cyclopentene derivatives in both high yields and diastereoselectivities, with enantiomeric excesses of up to 97 %.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allenoates; cyclizations; enantioselectivity; organocatalysis; phosphahelicene

Year:  2015        PMID: 25753678     DOI: 10.1002/anie.201500299

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


  9 in total

1.  Phosphahelicenes: From Chiroptical and Photophysical Properties to OLED Applications.

Authors:  Keihann Yavari; Wylliam Delaunay; Nicolas De Rycke; Thibault Reynaldo; Paul Aillard; Monika Srebro-Hooper; Victoria Y Chang; Gilles Muller; Denis Tondelier; Bernard Geffroy; Arnaud Voituriez; Angela Marinetti; Muriel Hissler; Jeanne Crassous
Journal:  Chemistry       Date:  2019-03-12       Impact factor: 5.236

Review 2.  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

3.  Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.

Authors:  Yumei Xiao; Hongchao Guo; Ohyun Kwon
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

4.  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

5.  Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines: a facile synthesis of tetrahydropyridines.

Authors:  Leijie Zhou; Chunhao Yuan; Yuan Zeng; Honglei Liu; Chang Wang; Xing Gao; Qijun Wang; Cheng Zhang; Hongchao Guo
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

6.  Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates.

Authors:  Andreas Eitzinger; Katharina Zielke; Michael Widhalm; Raphaël Robiette; Mario Waser
Journal:  Asian J Org Chem       Date:  2018-05-04       Impact factor: 3.319

7.  Asymmetric cyanation of imines via dipeptide-derived organophosphine dual-reagent catalysis.

Authors:  Hong-Yu Wang; Chang-Wu Zheng; Zhuo Chai; Jia-Xing Zhang; Gang Zhao
Journal:  Nat Commun       Date:  2016-09-14       Impact factor: 14.919

8.  Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones.

Authors:  Guo-Peng Wang; Yao-Liang Sun; Shou-Fei Zhu; Yin Wei; Qi-Lin Zhou; Min Shi
Journal:  Chem Sci       Date:  2015-09-15       Impact factor: 9.825

9.  Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones via regiodivergent [3 + 2] annulations of aurones and an allenoate.

Authors:  Huanzhen Ni; Zhaoyuan Yu; Weijun Yao; Yu Lan; Nisar Ullah; Yixin Lu
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825

  9 in total

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