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 Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes.

Literature DB >> 26244235

Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes.

Christopher Sandford¹, Ramesh Rasappan¹, Varinder K Aggarwal¹.

Abstract

The enantiospecific conversion of chiral secondary boronic esters into alkylfluorides is reported. Boronate complexes derived from boronic esters and PhLi were used as nucleophiles, with Selectfluor II as the electrophilic fluorinating agent, to afford alkylfluorides in short reaction times. The addition of styrene as a radical trap was found to enhance enantiospecificity. A broad range of alkyl boronic esters were converted into alkylfluorides with almost complete enantiospecificity by this method.

Entities: Chemical

Mesh：

Substances：

Year: 2015 PMID： 26244235 DOI： 10.1021/jacs.5b05848

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

Keyword Cloud
Cited

21 in total

Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes.

1. A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

2. Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

3. Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

4. Cu-Catalyzed Cross-Coupling of Benzylboronic Esters and Epoxides.

5. Benzylation of Imines with Activated Boronate Nucleophiles.

6. Nucleophilic Addition of Benzylboronates to Activated Ketones.

7. Synthesis of α-Fluoro-α-Amino Acid Derivatives via Photoredox-Catalyzed Carbofluorination.

8. Enantio- and Diastereoselective, Complete Hydrogenation of Benzofurans by Cascade Catalysis.

9. Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters.

10. Catalytic asymmetric nucleophilic fluorination using BF₃·Et₂O as fluorine source and activating reagent.