Literature DB >> 22789100

Asymmetric construction of functionalized bicyclic imides via [3 + 2] annulation of MBH carbonates catalyzed by dipeptide-based phosphines.

Fangrui Zhong1, Guo-Ying Chen, Xiaoyu Han, Weijun Yao, Yixin Lu.   

Abstract

A highly enantioselective [3 + 2] annulation of MBH carbonates and maleimides catalyzed by chiral phosphines has been developed. In the presence of 5 mol % of L-Thr-L-Val-derived phosphine 6, functionalized bicyclic imides were prepared in excellent yields, and with high diastereoselectivities and nearly perfect enantioselectivities.

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Year:  2012        PMID： 22789100     DOI： 10.1021/ol301647g

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


  7 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.  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

3.  Direct access to tetrasubstituted cyclopentenyl scaffolds through a diastereoselective isocyanide-based multicomponent reaction.

Authors:  Vitor A Fernandes; Rafaely N Lima; Yoisel B Broterson; Meire Y Kawamura; Radell Echemendía; Alexander F de la Torre; Marco A B Ferreira; Daniel G Rivera; Marcio W Paixão
Journal:  Chem Sci       Date:  2021-09-16       Impact factor: 9.825

Review 4.  Chiral phosphines in nucleophilic organocatalysis.

Authors:  Yumei Xiao; Zhanhu Sun; Hongchao Guo; Ohyun Kwon
Journal:  Beilstein J Org Chem       Date:  2014-09-04       Impact factor: 2.883

5.  Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine.

Authors:  Huanzhen Ni; Weijun Yao; Yixin Lu
Journal:  Beilstein J Org Chem       Date:  2016-02-24       Impact factor: 2.883

6.  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

7.  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
  7 in total

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