Literature DB >> 33665590

Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.

Hillary J Dequina1, Jennifer M Schomaker1.   

Abstract

Harnessing the chemistry of onium ylide intermediates generated from transition n class="Chemical">metal catalysis is a powerful strategy to convert simple precursors into complex scaffolds. While the chemistry of onium ylides has been studied for over three decades, transformations of aziridinium ylides have just recently emerged as a versatile way to exploit the strain of these reactive intermediates to furnish densely functionalized N-heterocycles in a highly stereocontrolled manner. Herein, we provide a short overview of the key concepts and recent developments in this area, with a focus on how mechanistic studies to delineate the factors controlling the reactivity of aziridinium ylides can stimulate fruitful future investigations.

Entities:  

Keywords:  aziridine; carbene transfer; cheletropic extrusion; ring expansion; ylide

Year:  2020        PMID: 33665590      PMCID: PMC7929518          DOI: 10.1016/j.trechm.2020.08.003

Source DB:  PubMed          Journal:  Trends Chem        ISSN: 2589-5974


  59 in total

1.  1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.

Authors:  Jared W Rigoli; Luke A Boralsky; John C Hershberger; Dagmara Marston; Alan R Meis; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2012-02-14       Impact factor: 4.354

2.  Rh2(R-TPCP)4-catalyzed enantioselective [3+2]-cycloaddition between nitrones and vinyldiazoacetates.

Authors:  Changming Qin; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2013-09-20       Impact factor: 15.419

3.  Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles.

Authors:  Stepan Chuprakov; Frank W Hwang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Rh2(S-biTISP)2-catalyzed asymmetric functionalization of indoles and pyrroles with vinylcarbenoids.

Authors:  Yajing Lian; Huw M L Davies
Journal:  Org Lett       Date:  2012-03-27       Impact factor: 6.005

5.  Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles.

Authors:  Tony Horneff; Stepan Chuprakov; Natalia Chernyak; Vladimir Gevorgyan; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

6.  Iron-catalyzed [3 + 2]-cycloaddition of in situ generated N-ylides with alkynes or olefins: access to multi-substituted/polycyclic pyrrole derivatives.

Authors:  Kai Zhou; Ming Bao; Jingjing Huang; Zhenghui Kang; Xinfang Xu; Wenhao Hu; Yu Qian
Journal:  Org Biomol Chem       Date:  2020-01-22       Impact factor: 3.876

7.  Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines.

Authors:  V Helan; A V Gulevich; V Gevorgyan
Journal:  Chem Sci       Date:  2015-03       Impact factor: 9.825

8.  Ammonium Ylide Mediated Cyclization Reactions.

Authors:  Lukas Roiser; Katharina Zielke; Mario Waser
Journal:  Asian J Org Chem       Date:  2018-03-25       Impact factor: 3.319

9.  Intermolecular [3+3] ring expansion of aziridines to dehydropiperi-dines through the intermediacy of aziridinium ylides.

Authors:  Josephine Eshon; Kate A Nicastri; Steven C Schmid; William T Raskopf; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  Nat Commun       Date:  2020-03-09       Impact factor: 14.919

10.  Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C-H insertion of donor/donor carbenes.

Authors:  Leslie A Nickerson; Benjamin D Bergstrom; Mingchun Gao; Yuan-Shin Shiue; Croix J Laconsay; Matthew R Culberson; Walker A Knauss; James C Fettinger; Dean J Tantillo; Jared T Shaw
Journal:  Chem Sci       Date:  2019-11-13       Impact factor: 9.825

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  3 in total

1.  Tunable Aziridinium Ylide Reactivity: Non-covalent Interactions Enable Divergent Product Outcomes.

Authors:  Kate A Nicastri; Soren Zappia; Jared C Pratt; Julia M Duncan; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  ACS Catal       Date:  2022-01-11       Impact factor: 13.084

2.  Biocatalytic One-Carbon Ring Expansion of Aziridines to Azetidines via a Highly Enantioselective [1,2]-Stevens Rearrangement.

Authors:  David C Miller; Ravi G Lal; Luca A Marchetti; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2022-03-08       Impact factor: 16.383

Review 3.  Synthetic Applications of Aziridinium Ions.

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

  3 in total

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