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Literature DB >> 29024289

Diastereoselective C-H Bond Amination for Disubstituted Pyrrolidines.

Diana A Iovan¹, Matthew J T Wilding¹, Yunjung Baek¹, Elisabeth T Hennessy¹, Theodore A Betley¹.

Abstract

We report herein the improved diastereoselective synthesis of 2,5-disubstituted pyrrolidines from aliphatic azides. Experimental and theoretical studies of the C-H amination reaction mediated by the iron dipyrrinato complex (Ad L)FeCl(OEt2 ) provided a model for diastereoinduction and allowed for systematic variation of the catalyst to enhance selectivity. Among the iron alkoxide and aryloxide catalysts evaluated, the iron phenoxide complex exhibited superior performance towards the generation of syn 2,5-disubstituted pyrrolidines with high diastereoselectivity.

Entities: CellLine Chemical Disease Gene

Keywords: C−H activation; diastereoselectivity; iron; phenoxide; pyrrolidine

Mesh：

Substances：

Year: 2017 PMID： 29024289 PMCID： PMC5821116 DOI： 10.1002/anie.201708519

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

26 in total

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2. 2,5-Disubstituted pyrrolidines: synthesis by enamine reduction and subsequent regioselective and diastereoselective alkylations.

Authors: Syed Raziullah Hussaini; Mark G Moloney
Journal: Org Biomol Chem Date: 2006-05-31 Impact factor: 3.876

3. Cardiovascular effects of lepadiformine, an alkaloid isolated from the ascidians Clavelina lepadiformis (Müller) and C. moluccensis (Sluiter).

Authors: M Jugé; N Grimaud; J F Biard; M P Sauviat; M Nabil; J F Verbist; J Y Petit
Journal: Toxicon Date: 2001-08 Impact factor: 3.033

4. A diruthenium catalyst for selective, intramolecular allylic C-H amination: reaction development and mechanistic insight gained through experiment and theory.

Authors: Mark Edwin Harvey; Djamaladdin G Musaev; J Du Bois
Journal: J Am Chem Soc Date: 2011-10-07 Impact factor: 15.419

5. Asymmetric total synthesis of (+)-merobatzelladine B.

Authors: Nicholas R Babij; John P Wolfe
Journal: Angew Chem Int Ed Engl Date: 2012-03-16 Impact factor: 15.336

6. Palladium-catalyzed asymmetric [3 + 2] trimethylenemethane cycloaddition reactions.

Authors: Barry M Trost; James P Stambuli; Steven M Silverman; Ulrike Schwörer
Journal: J Am Chem Soc Date: 2006-10-18 Impact factor: 15.419

7. Pd-catalyzed carboamination of oxazolidin-2-ones: a stereoselective route to trans-2,5-disubstituted pyrrolidines.

Authors: Georgia S Lemen; John P Wolfe
Journal: Org Lett Date: 2010-05-21 Impact factor: 6.005

8. Catalytic C-H bond amination from high-spin iron imido complexes.

Authors: Evan R King; Elisabeth T Hennessy; Theodore A Betley
Journal: J Am Chem Soc Date: 2011-03-15 Impact factor: 15.419

9. Ground State and Excited State Tuning in Ferric Dipyrrin Complexes Promoted by Ancillary Ligand Exchange.

Authors: Claudia Kleinlein; Shao-Liang Zheng; Theodore A Betley
Journal: Inorg Chem Date: 2017-04-24 Impact factor: 5.165

10. Asymmetric synthesis of trans-2,5-disubstituted pyrrolidines from enantiopure homoallylic amines. Synthesis of pyrrolidine (-)-197B.

Authors: Franklin A Davis; Minsoo Song; Alexander Augustine
Journal: J Org Chem Date: 2006-03-31 Impact factor: 4.354

11 in total

1. Oxidative nitrene transfer from azides to alkynes via Ti(ii)/Ti(iv) redox catalysis: formal [2+2+1] synthesis of pyrroles.

Authors: Adam J Pearce; Xin Yi See; Ian A Tonks
Journal: Chem Commun (Camb) Date: 2018-06-19 Impact factor: 6.222

2. Catalytic C-H Amination Mediated by Dipyrrin Cobalt Imidos.

Authors: Yunjung Baek; Theodore A Betley
Journal: J Am Chem Soc Date: 2019-05-07 Impact factor: 15.419

3. O-Heterocycle Synthesis via Intramolecular C-H Alkoxylation Catalyzed by Iron Acetylacetonate.

Authors: Yuyang Dong; Alexandra T Wrobel; Gerard J Porter; Jessica J Kim; Jake Z Essman; Shao-Liang Zheng; Theodore A Betley
Journal: J Am Chem Soc Date: 2021-05-05 Impact factor: 16.383

4. C-H Amination Mediated by Cobalt Organoazide Adducts and the Corresponding Cobalt Nitrenoid Intermediates.

Authors: Yunjung Baek; Anuvab Das; Shao-Liang Zheng; Joseph H Reibenspies; David C Powers; Theodore A Betley
Journal: J Am Chem Soc Date: 2020-06-12 Impact factor: 16.383

5. [2Fe-2S] Cluster Supported by Redox-Active o-Phenylenediamide Ligands and Its Application toward Dinitrogen Reduction.

Authors: Qiuming Liang; Joshua C DeMuth; Aleksa Radović; Nikki J Wolford; Michael L Neidig; Datong Song
Journal: Inorg Chem Date: 2021-05-27 Impact factor: 5.436