Literature DB >> 29728870

Nucleophilic ring opening reactions of aziridines.

Rabia Akhtar1, Syed Ali Raza Naqvi1, Ameer Fawad Zahoor2, Sameera Saleem1.   

Abstract

Aziridine ring opening reactions have gained tremendous importance in the synthesis of nitrogen containing biologically active molecules. During recent years, a great effort has been put forward by scientists toward unique bond construction methodologies via ring opening of aziridines. In this regard, a wide range of chiral metal- and organo-catalyzed desymmetrization reactions of aziridines have been reported with carbon, sulfur, oxygen, nitrogen, halogen, and other nucleophiles. In this review, an outline of methodologies adopted by a number of scientists during 2013-2017 for aziridine ring opening reactions as well as their synthetic applications is described.

Entities:  

Keywords:  Aziridine; Biologically active compounds; Enantioselective synthesis; Methodology development; Ring opening reactions

Mesh:

Substances:

Year:  2018        PMID: 29728870     DOI: 10.1007/s11030-018-9829-0

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  64 in total

1.  Enantiopure Trans-4,5-Disubstituted 2-Imidazolidinones via Copper(I)-Catalyzed Ring Opening of 1,1'-DiBoc-2,2'-Biaziridine with Grignard Reagents.

Authors:  Matthew D Kennedy; Stephen J Bailey; Steven M Wales; Paul A Keller
Journal:  J Org Chem       Date:  2015-05-07       Impact factor: 4.354

2.  Palladium-mediated annulation of vinyl aziridines with Michael acceptors: stereocontrolled synthesis of substituted pyrrolidines and its application in a formal synthesis of (-)-α-kainic acid.

Authors:  Martin A Lowe; Mehrnoosh Ostovar; Serena Ferrini; C Chun Chen; Paul G Lawrence; Francesco Fontana; Andrew A Calabrese; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-27       Impact factor: 15.336

3.  A novel and selective fluoride opening of aziridines by XtalFluor-E. synthesis of fluorinated diamino acid derivatives.

Authors:  Melinda Nonn; Loránd Kiss; Matti Haukka; Santos Fustero; Ferenc Fülöp
Journal:  Org Lett       Date:  2015-02-16       Impact factor: 6.005

4.  A novel Lewis acid catalyzed [3 + 3]-annulation strategy for the syntheses of tetrahydro-β-carbolines and tetrahydroisoquinolines.

Authors:  Shaoyin Wang; Zhuo Chai; Shuangliu Zhou; Shaowu Wang; Xiancui Zhu; Yun Wei
Journal:  Org Lett       Date:  2013-05-10       Impact factor: 6.005

5.  Synthesis of trifluoromethyl γ-aminophosphonates by nucleophilic aziridine ring opening.

Authors:  T Cytlak; M Saweliew; M Kubicki; H Koroniak
Journal:  Org Biomol Chem       Date:  2015-10-21       Impact factor: 3.876

6.  Hexafluoroantimonic acid catalysis: formal [3+2+2] cycloaddition of aziridines with two alkynes.

Authors:  Ming-Bo Zhou; Ren-Jie Song; Jin-Heng Li
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-11       Impact factor: 15.336

7.  Enantioselective synthesis of 4,5-dihydropyrroles via domino ring-opening cyclization (DROC) of N-activated aziridines with malononitrile.

Authors:  Manas K Ghorai; Deo Prakash Tiwari
Journal:  J Org Chem       Date:  2013-02-19       Impact factor: 4.354

8.  Desymmetrization of meso-aziridines with TMSNCS using metal salts of novel chiral imidazoline-phosphoric acid catalysts.

Authors:  Shuichi Nakamura; Mutsuyo Ohara; Madoka Koyari; Masashi Hayashi; Kengo Hyodo; Nadaf Rashid Nabisaheb; Yasuhiro Funahashi
Journal:  Org Lett       Date:  2014-08-08       Impact factor: 6.005

9.  Synthesis of N-Aryl β-Amino Alcohols by Trifluoroacetic Acid Promoted Multicomponent Coupling of Aziridines, Arynes, and Water.

Authors:  Tony Roy; Dnyaneshwar R Baviskar; Akkattu T Biju
Journal:  J Org Chem       Date:  2015-10-15       Impact factor: 4.354

10.  Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines.

Authors:  Ashley N Jarvis; Andrew B McLaren; Helen M I Osborn; Joseph Sweeney
Journal:  Beilstein J Org Chem       Date:  2013-05-02       Impact factor: 2.883

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  7 in total

1.  Palladium-Catalyzed, Enantioselective Desymmetrization of N-Acylaziridines with Indoles.

Authors:  Kinney Van Hecke; Tyler R Benton; Michael Casper; Dustin Mauldin; Brandon Drake; Jeremy B Morgan
Journal:  Org Lett       Date:  2021-10-05       Impact factor: 6.072

Review 2.  N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds.

Authors:  Iwona E Głowacka; Aleksandra Trocha; Andrzej E Wróblewski; Dorota G Piotrowska
Journal:  Beilstein J Org Chem       Date:  2019-07-23       Impact factor: 2.883

Review 3.  Synthetically important ring opening reactions by alkoxybenzenes and alkoxynaphthalenes.

Authors:  Ranadeep Talukdar
Journal:  RSC Adv       Date:  2020-08-25       Impact factor: 4.036

4.  Toward asymmetric aziridination with an iron complex supported by a D2-symmetric tetra-NHC.

Authors:  Kevin M Blatchford; Carson J Mize; Sharani Roy; David M Jenkins
Journal:  Dalton Trans       Date:  2022-04-20       Impact factor: 4.569

5.  Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with β-Keto Esters.

Authors:  Victoria Haider; Viktoria Kreuzer; Maximilian Tiffner; Bernhard Spingler; Mario Waser
Journal:  European J Org Chem       Date:  2020-07-15

Review 6.  Synthetic Applications of Aziridinium Ions.

Authors:  Jala Ranjith; Hyun-Joon Ha
Journal:  Molecules       Date:  2021-03-22       Impact factor: 4.411

Review 7.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823

  7 in total

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