Literature DB >> 27005726

Asymmetric preparation of polysubstituted cyclopentanes by synergistic Pd(0)/amine catalyzed formal [3+2] cycloadditions of vinyl cyclopropanes with enals.

Maxime Laugeois1, Sudipta Ponra, Virginie Ratovelomanana-Vidal, Véronique Michelet, Maxime R Vitale.   

Abstract

We report herein a novel diastereo- and enantiocontrolled preparation of polysubstituted cyclopentanes by the formal [3+2] cycloadditions of vinyl cyclopropanes with enals. In constrast with previously developed strategies, our original approach is based on the synergistic merger of iminium/enamine organocatalysis with palladium(0) catalysis.

Entities:  

Year:  2016        PMID： 27005726     DOI： 10.1039/c6cc01775d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  7 in total

1.  Palladium-Catalyzed Cascade to Benzoxepins by Using Vinyl-Substituted Donor-Acceptor Cyclopropanes.

Authors:  Matteo Faltracco; Koen N A van de Vrande; Martijn Dijkstra; Jordy M Saya; Trevor A Hamlin; Eelco Ruijter
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-26       Impact factor: 15.336

2.  Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals.

Authors:  Haipan Zhu; Peile Du; Jianjun Li; Ziyang Liao; Guohua Liu; Hao Li; Wei Wang
Journal:  Beilstein J Org Chem       Date:  2016-06-29       Impact factor: 2.883

3.  Synergistic formal ring contraction for the enantioselective synthesis of spiropyrazolones.

Authors:  Marta Meazza; Martin Kamlar; Lucie Jašíková; Bedřich Formánek; Andrea Mazzanti; Jana Roithová; Jan Veselý; Ramon Rios
Journal:  Chem Sci       Date:  2018-06-28       Impact factor: 9.825

Review 4.  Recent progress in asymmetric synergistic catalysis - the judicious combination of selected chiral aminocatalysts with achiral metal catalysts.

Authors:  Christian D-T Nielsen; Joshua D Linfoot; Alexander F Williams; Alan C Spivey
Journal:  Org Biomol Chem       Date:  2022-04-06       Impact factor: 3.890

5.  Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides.

Authors:  Yan Lin; Qijun Wang; Yang Wu; Chang Wang; Hao Jia; Cheng Zhang; Jiaxing Huang; Hongchao Guo
Journal:  RSC Adv       Date:  2018-12-05       Impact factor: 3.361

6.  Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.

Authors:  Jacqueline Bitai; Alastair J Nimmo; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-28       Impact factor: 16.823

7.  Pot and time economies in the total synthesis of Corey lactone.

Authors:  Nariyoshi Umekubo; Yurina Suga; Yujiro Hayashi
Journal:  Chem Sci       Date:  2019-12-23       Impact factor: 9.825
  7 in total

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