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Literature DB >> 22489747

Synthesis of β-fluoroamines by Lewis base catalyzed hydrofluorination of aziridines.

Julia A Kalow¹, Dana E Schmitt, Abigail G Doyle.

Abstract

Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide β-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant β-fluoroamine building blocks are presented.

Entities: Chemical

Mesh：

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Year: 2012 PMID： 22489747 DOI： 10.1021/jo300433a

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

8 in total

1. Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.

Authors: Brandon A Vara; Jeffrey N Johnston
Journal: J Am Chem Soc Date: 2016-10-17 Impact factor: 15.419

2. Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

Authors: Sota Akiyama; Koji Kubota; Malte S Mikus; Paulo H S Paioti; Filippo Romiti; Qinghe Liu; Yuebiao Zhou; Amir H Hoveyda; Hajime Ito
Journal: Angew Chem Int Ed Engl Date: 2019-07-16 Impact factor: 15.336

3. Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions.

Authors: Otome E Okoromoba; Zhou Li; Nicole Robertson; Mark S Mashuta; Uenifer R Couto; Cláudio F Tormena; Bo Xu; Gerald B Hammond
Journal: Chem Commun (Camb) Date: 2016-11-08 Impact factor: 6.222

4. Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

Authors: Deng-Fu Lu; Cheng-Liang Zhu; Jeffrey D Sears; Hao Xu
Journal: J Am Chem Soc Date: 2016-08-26 Impact factor: 15.419

5. A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.

Authors: Jeffrey Wu; Yi-Ming Wang; Amela Drljevic; Vivek Rauniyar; Robert J Phipps; F Dean Toste
Journal: Proc Natl Acad Sci U S A Date: 2013-08-06 Impact factor: 11.205

Synthesis of β-fluoroamines by Lewis base catalyzed hydrofluorination of aziridines.

1. Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.

2. Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

3. Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions.

4. Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

5. A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.

6. A general, enantioselective synthesis of β- and γ-fluoroamines.

7. Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion.

Review 8. Organocatalyzed enantioselective desymmetrization of aziridines and epoxides.