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Literature DB >> 11869147

Amidoglycosylation via metal-catalyzed internal nitrogen atom delivery.

Elana Levites-Agababa¹, Elnaz Menhaji, Lisa N Perlson, Christian M Rojas.

Abstract

[reaction: see text] Rhodium and copper acyl nitrenoids are likely intermediates in amidoglycosylation reactions of allal 3-carbamates. Iodine(III)-mediated nitrenoid formation, interaction of this species with the glycal enol ether pi-system, and highly beta-stereoselective glycosylation occur in a one-pot process that requires no additional Lewis acid activation.

Entities: Chemical

Mesh：

Substances：

Year: 2002 PMID： 11869147 DOI： 10.1021/ol025634k

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

9 in total

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

Authors: Huiling Jiang; Kai Lang; Hongjian Lu; Lukasz Wojtas; X Peter Zhang
Journal: J Am Chem Soc Date: 2017-06-29 Impact factor: 15.419

2. 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

9. Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines.

Authors: Deng-Fu Lu; Cheng-Liang Zhu; Zhen-Xin Jia; Hao Xu
Journal: J Am Chem Soc Date: 2014-09-16 Impact factor: 15.419

9 in total

Amidoglycosylation via metal-catalyzed internal nitrogen atom delivery.

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

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

3. Dihydropyranone formation by ipso C-H activation in a glucal 3-carbamate-derived rhodium acyl nitrenoid.

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

5. Iron catalyzed asymmetric oxyamination of olefins.

6. Protecting group and solvent control of stereo- and chemoselectivity in glucal 3-carbamate amidoglycosylation.

Review 7. One-pot construction of carbohydrate scaffolds mediated by metal catalysts.

8. 1,2-Amino oxygenation of alkenes with hydrogen evolution reaction.

9. Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines.