Literature DB >> 24737675

Asymmetric synthesis of spiropyrazolones through phosphine-catalyzed [4+1] annulation.

Xiaoyu Han1, Weijun Yao, Tianli Wang, Yong Ren Tan, Ziyu Yan, Jacek Kwiatkowski, Yixin Lu.   

Abstract

An enantioselective synthesis of spiropyrazolones from allenoate-derived MBH acetates and pyrazolones through a phosphine-mediated [4+1] annulation process has been developed. Spiropyrazolones were readily prepared in good chemical yields and good to high enantioselectivities. This is the first asymmetric example in which α-substituted allenoates were utilized as a C4 synthon for phosphine-catalyzed [4+1] annulation.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  [4+1] annulation; allenoates; chiral phosphines; spiro compounds; spiropyrazolones

Mesh：

Substances：

Year:  2014        PMID： 24737675     DOI： 10.1002/anie.201311214

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


  17 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.  Use of a new spirophosphine to achieve catalytic enantioselective [4 + 1] annulations of amines with allenes to generate dihydropyrroles.

Authors:  Søren Kramer; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2015-03-17       Impact factor: 15.419

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.  Biphenyl-derived phosphepines as chiral nucleophilic catalysts: enantioselective [4+1] annulations to form functionalized cyclopentenes.

Authors:  Daniel T Ziegler; Lorena Riesgo; Takuya Ikeda; Yuji Fujiwara; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-06       Impact factor: 15.336

5.  Formal (4 + 1)-Addition of Allenoates to o-Quinone Methides.

Authors:  Katharina Zielke; Mario Waser
Journal:  Org Lett       Date:  2018-01-19       Impact factor: 6.005

6.  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

7.  An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.

Authors:  Kevin X Rodriguez; Tara C Pilato; Brandon L Ashfeld
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

8.  Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis.

Authors:  Daniel Hack; Alexander B Dürr; Kristina Deckers; Pankaj Chauhan; Nico Seling; Lukas Rübenach; Lucas Mertens; Gerhard Raabe; Franziska Schoenebeck; Dieter Enders
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-16       Impact factor: 15.336

9.  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

10.  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
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