Literature DB >> 26311134

Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide-alkyne cycloadditions.

William D G Brittain1, Benjamin R Buckley2, John S Fossey1.   

Abstract

The synthesis and kinetic resolution of quaternary oxindoles through copper catalysed azide-alkyne cycloadditions is presented. Selectivity factors (s) up to 22.1 ± 0.5 are reported. Enantioenriched alkynes and triazoles were obtained in ≥80% enantiomeric excess (e.e.).

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Year:  2015        PMID： 26311134     DOI： 10.1039/c5cc04886a

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


  10 in total

1.  Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.

Authors:  En-Chih Liu; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2019-03-21       Impact factor: 15.419

2.  Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition.

Authors:  Juliana R Alexander; Amy A Ott; En-Chih Liu; Joseph J Topczewski
Journal:  Org Lett       Date:  2019-05-22       Impact factor: 6.005

3.  The Bull-James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction.

Authors:  William D G Brittain; Brette M Chapin; Wenlei Zhai; Vincent M Lynch; Benjamin R Buckley; Eric V Anslyn; John S Fossey
Journal:  Org Biomol Chem       Date:  2016-11-22       Impact factor: 3.876

Review 4.  Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring.

Authors:  Eszter Kókai; Gyula Simig; Balázs Volk
Journal:  Molecules       Date:  2016-12-26       Impact factor: 4.411

5.  Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling.

Authors:  Yiming Zhao; Huy van Nguyen; Louise Male; Philip Craven; Benjamin R Buckley; John S Fossey
Journal:  Organometallics       Date:  2018-10-17       Impact factor: 3.876

6.  Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation.

Authors:  William D G Brittain; Andrew G Dalling; Zhenquan Sun; Cécile S Le Duff; Louise Male; Benjamin R Buckley; John S Fossey
Journal:  Sci Rep       Date:  2019-10-21       Impact factor: 4.379

7.  Electrochemical Umpolung C-H Functionalization of Oxindoles.

Authors:  Miryam Pastor; Marie Vayer; Harald Weinstabl; Nuno Maulide
Journal:  J Org Chem       Date:  2021-12-28       Impact factor: 4.354

8.  Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis.

Authors:  Akina Yoshizawa; Antonio Feula; Louise Male; Andrew G Leach; John S Fossey
Journal:  Sci Rep       Date:  2018-04-25       Impact factor: 4.379

9.  Enantioselective synthesis of P-chiral tertiary phosphine oxides with an ethynyl group via Cu(i)-catalyzed azide-alkyne cycloaddition.

Authors:  Ren-Yi Zhu; Long Chen; Xiao-Si Hu; Feng Zhou; Jian Zhou
Journal:  Chem Sci       Date:  2019-11-06       Impact factor: 9.825

10.  Derivatisation of parthenolide to address chemoresistant chronic lymphocytic leukaemia.

Authors:  Xingjian Li; Daniel T Payne; Badarinath Ampolu; Nicholas Bland; Jane T Brown; Mark J Dutton; Catherine A Fitton; Abigail Gulliver; Lee Hale; Daniel Hamza; Geraint Jones; Rebecca Lane; Andrew G Leach; Louise Male; Elena G Merisor; Michael J Morton; Alex S Quy; Ruth Roberts; Rosanna Scarll; Timothy Schulz-Utermoehl; Tatjana Stankovic; Brett Stevenson; John S Fossey; Angelo Agathanggelou
Journal:  Medchemcomm       Date:  2019-08-01       Impact factor: 3.597
  10 in total

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