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Literature DB >> 19123840

Instantaneous deprotection of tosylamides and esters with SmI(2)/amine/water.

Abstract

SmI(2)/amine/water mediates instantaneous cleavage of tosyl amides and tosyl esters. Highly hindered, sensitive and functionalized substrates were successfully deprotected in near quantitative yield.

Entities: Chemical

Year: 2009 PMID： 19123840 DOI： 10.1021/ol802243d

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

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Cited

17 in total

1. Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.

Authors: Qilei Zhu; David E Graff; Robert R Knowles
Journal: J Am Chem Soc Date: 2018-01-04 Impact factor: 15.419

2. Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer.

Authors: Ke Kong; Ziad Moussa; Changsuk Lee; Daniel Romo
Journal: J Am Chem Soc Date: 2011-11-16 Impact factor: 15.419

3. Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme.

Authors: Christopher K Prier; Ruijie K Zhang; Andrew R Buller; Sabine Brinkmann-Chen; Frances H Arnold
Journal: Nat Chem Date: 2017-05-29 Impact factor: 24.427

4. CdS Quantum Dots as Potent Photoreductants for Organic Chemistry Enabled by Auger Processes.

Authors: Jonas K Widness; Daniel G Enny; Kaelyn S McFarlane-Connelly; Mahilet T Miedenbauer; Todd D Krauss; Daniel J Weix
Journal: J Am Chem Soc Date: 2022-06-30 Impact factor: 16.383

5. Synthesis of Agelastatin A and Derivatives Premised on a Hidden Symmetry Element Leading to Analogs Displaying Anticancer Activity.

Authors: Haoran Xue; Haleigh Svatek; Ariane F Bertonha; Keighley Reisenauer; Joshua Robinson; Minwoo Kim; Alec Ingros; Matthew Ho; Joseph Taube; Daniel Romo
Journal: Tetrahedron Date: 2021-07-10 Impact factor: 2.388

10. Synthesis and biological activity of conformationally restricted indole-based inhibitors of neurotropic alphavirus replication: Generation of a three-dimensional pharmacophore.

Authors: Scott J Barraza; Janice A Sindac; Craig J Dobry; Philip C Delekta; Pil H Lee; David J Miller; Scott D Larsen
Journal: Bioorg Med Chem Lett Date: 2021-06-15 Impact factor: 2.940

Instantaneous deprotection of tosylamides and esters with SmI(2)/amine/water.

1. Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.

2. Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer.

3. Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme.

4. CdS Quantum Dots as Potent Photoreductants for Organic Chemistry Enabled by Auger Processes.

5. Synthesis of Agelastatin A and Derivatives Premised on a Hidden Symmetry Element Leading to Analogs Displaying Anticancer Activity.

6. N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines.

7. Traceless Benzylic C-H Amination via Bifunctional N-Aminopyridinium Intermediates.

8. 3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.

9. Metalloradical activation of carbonyl azides for enantioselective radical aziridination.

10. Synthesis and biological activity of conformationally restricted indole-based inhibitors of neurotropic alphavirus replication: Generation of a three-dimensional pharmacophore.