Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Asymmetric Radical Bicyclization of Allyl Azidoformates via Cobalt(II)-Based Metalloradical Catalysis.

Literature DB >> 28650659

Asymmetric Radical Bicyclization of Allyl Azidoformates via Cobalt(II)-Based Metalloradical Catalysis.

Huiling Jiang¹, Kai Lang², Hongjian Lu¹, Lukasz Wojtas¹, X Peter Zhang^2,1.

Abstract

Cobalt(II)-based metalloradical catalysis has been successfully applied to radical bicyclization of allyl azidoformates to construct aziridine/oxazolidinone-fused bicyclic structures. The Co(II) complex of D2-symmetric chiral amidoporphyrin 3,5-DitBu-QingPhyrin has been identified as an effective metalloradical catalyst for the intramolecular radical aziridination of this type of carbonyl azides, allowing for high-yielding formation of synthetically useful chiral [3.1.0]-bicyclic aziridines with high diastereo- and enantioselectivity.

Entities: CellLine Chemical Disease Gene

Mesh：

Substances：

Year: 2017 PMID： 28650659 PMCID： PMC5553632 DOI： 10.1021/jacs.7b05778

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

58 in total

1. Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors: Paul Müller; Corinne Fruit
Journal: Chem Rev Date: 2003-08 Impact factor: 60.622

2. A radical tandem reaction with homolytic cleavage of a Ti-O bond.

Authors: Andreas Gansäuer; Björn Rinker; Marianna Pierobon; Stefan Grimme; Mareike Gerenkamp; Christian Mück-Lichtenfeld
Journal: Angew Chem Int Ed Engl Date: 2003-08-11 Impact factor: 15.336

3. Tuning the redox properties of the titanocene(III)/(IV)-couple for atom-economical catalysis in single electron steps.

Authors: A Gansäuer; S Hildebrandt; E Vogelsang; R A Flowers Ii
Journal: Dalton Trans Date: 2016-01-14 Impact factor: 4.390

Review 4. Catalysis of Radical Reactions: A Radical Chemistry Perspective.

Authors: Armido Studer; Dennis P Curran
Journal: Angew Chem Int Ed Engl Date: 2015-10-13 Impact factor: 15.336

5. Enantioselective cobalt-catalyzed transformations.

Authors: Hélène Pellissier; Hervé Clavier
Journal: Chem Rev Date: 2014-01-15 Impact factor: 60.622

Review 6. Recent advances in the stereoselective synthesis of aziridines.

Authors: Leonardo Degennaro; Piera Trinchera; Renzo Luisi
Journal: Chem Rev Date: 2014-05-13 Impact factor: 60.622

7. Enantioselective synthesis of an ophiobolin sesterterpene via a programmed radical cascade.

Authors: Zachary G Brill; Huck K Grover; Thomas J Maimone
Journal: Science Date: 2016-05-27 Impact factor: 47.728

8. Recent advances in transition metal-catalyzed N-atom transfer reactions of azides.

Authors: Tom G Driver
Journal: Org Biomol Chem Date: 2010-07-08 Impact factor: 3.876

9. Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening.

Authors: Stephen C. Bergmeier; Dionne M. Stanchina
Journal: J Org Chem Date: 1997-06-27 Impact factor: 4.354

Review 10. Selective functionalisation of saturated C-H bonds with metalloporphyrin catalysts.

Authors: Chi-Ming Che; Vanessa Kar-Yan Lo; Cong-Ying Zhou; Jie-Sheng Huang
Journal: Chem Soc Rev Date: 2011-03-09 Impact factor: 54.564

14 in total

1. Catalytic aziridination with alcoholic substrates via a chromium tetracarbene catalyst.

Authors: C Luke Keller; Jesse L Kern; Bradley D Terry; Sharani Roy; David M Jenkins
Journal: Chem Commun (Camb) Date: 2018-01-04 Impact factor: 6.222

2. Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution.

Authors: Kai Lang; Sebastian Torker; Lukasz Wojtas; X Peter Zhang
Journal: J Am Chem Soc Date: 2019-07-29 Impact factor: 15.419

3. Glycal Metallanitrenes for 2-Amino Sugar Synthesis: Amidoglycosylation of Gulal-, Allal-, Glucal-, and Galactal 3-Carbamates.

Authors: Simran Buttar; Julia Caine; Evelyne Goné; Reneé Harris; Jennifer Gillman; Roxanne Atienza; Ritu Gupta; Kimberly M Sogi; Lauren Jain; Nadia C Abascal; Yetta Levine; Lindsay M Repka; Christian M Rojas
Journal: J Org Chem Date: 2018-07-06 Impact factor: 4.354

4. Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.

Authors: Honghui Lei; John H Conway; Caleb C Cook; Tomislav Rovis
Journal: J Am Chem Soc Date: 2019-07-16 Impact factor: 15.419

5. Is the Electrophilicity of the Metal Nitrene the Sole Predictor of Metal-Mediated Nitrene Transfer to Olefins? Secondary Contributing Factors as Revealed by a Library of High-Spin Co(II) Reagents.

Authors: Anshika Kalra; Vivek Bagchi; Patrina Paraskevopoulou; Purak Das; Lin Ai; Yiannis Sanakis; Grigorios Raptopoulos; Sudip Mohapatra; Amitava Choudhury; Zhicheng Sun; Thomas R Cundari; Pericles Stavropoulos
Journal: Organometallics Date: 2021-06-04 Impact factor: 3.876

10. Revisiting the Electronic Structure of Cobalt Porphyrin Nitrene and Carbene Radicals with NEVPT2-CASSCF Calculations: Doublet versus Quartet Ground States.

Authors: Nicolaas P van Leest; Bas de Bruin
Journal: Inorg Chem Date: 2021-06-05 Impact factor: 5.165