Literature DB >> 25799312

Phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines.

Lei Zhang1, Honglei Liu1, Guanyu Qiao1, Zhanfeng Hou1, Yang Liu1, Yumei Xiao1, Hongchao Guo1.   

Abstract

The first phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines is described. Using a spirocyclic chiral phosphine as the catalyst, a novel class of pharmaceutically interesting 4,6,7,11b-tetrahydro-1H-pyridazino[6,1-a]iso-quinoline derivatives were obtained in high yields with good to excellent diastereoselectivities and extremely excellent enantioselectivities (98->99% ee).

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Year:  2015        PMID： 25799312     DOI： 10.1021/jacs.5b01138

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 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.  One-pot synthesis of novel 1-(1H-tetrazol-5-yl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives via an Ugi-azide 4CR process.

Authors:  Mehdi Ghandi; Saleh Salahi; Abuzar Taheri; Alireza Abbasi
Journal:  Mol Divers       Date:  2017-12-11       Impact factor: 2.943

4.  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

5.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036

6.  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

7.  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

8.  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

9.  Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones.

Authors:  Guipeng Feng; Guoyang Ma; Wenyan Chen; Shaohong Xu; Kaikai Wang; Shaoyan Wang
Journal:  Molecules       Date:  2021-05-17       Impact factor: 4.411

10.  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 in total

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