Literature DB >> 31338507

Aminophosphonates and aminophosphonic acids with tetrasubstituted stereogenic center: diastereoselective synthesis from cyclic ketimines.

Jakub Iwanejko1, Anna Brol, Bartłomiej M Szyja, Marek Daszkiewicz, Elżbieta Wojaczyńska, Tomasz K Olszewski.   

Abstract

New chiral tetrasubstituted aminophosphonic acid derivatives of hexahydroquinoxalin-2(1H)-one were synthesised via highly diastereoselective hydrophosphonylation of the corresponding imines with tris(trimethylsilyl) phosphite as phosphorus nucleophile. High asymmetric induction, good yields, mild reaction conditions, and ease of purification of the final products are the key advantages of the presented protocol.

Entities:  

Year:  2019        PMID: 31338507     DOI: 10.1039/c9ob01346f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  4 in total

1.  Cytotoxic Activity of Piperazin-2-One-Based Structures: Cyclic Imines, Lactams, Aminophosphonates, and Their Derivatives.

Authors:  Jakub Iwanejko; Mahzeiar Samadaei; Matthias Pinter; Daniel Senfter; Sibylle Madlener; Andrzej Kochel; Nataliya Rohr-Udilova; Elżbieta Wojaczyńska
Journal:  Materials (Basel)       Date:  2021-04-22       Impact factor: 3.623

2.  An approach to new chiral bicyclic imines and amines via Horner-Wadsworth-Emmons reaction.

Authors:  Jakub Iwanejko; Mateusz Sowiński; Elżbieta Wojaczyńska; Tomasz K Olszewski; Marcin Górecki
Journal:  RSC Adv       Date:  2020-04-09       Impact factor: 3.361

3.  Octahydroquinoxalin-2(1H)-One-Based Aminophosphonic Acids and Their Derivatives-Biological Activity Towards Cancer Cells.

Authors:  Jakub Iwanejko; Elżbieta Wojaczyńska; Eliza Turlej; Magdalena Maciejewska; Joanna Wietrzyk
Journal:  Materials (Basel)       Date:  2020-05-22       Impact factor: 3.623

Review 4.  Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives.

Authors:  Aitor Maestro; Xabier Del Corte; Adrián López-Francés; Edorta Martínez de Marigorta; Francisco Palacios; Javier Vicario
Journal:  Molecules       Date:  2021-05-27       Impact factor: 4.411

  4 in total

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