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Literature DB >> 25582419

A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.

Yan-Shuang Xu¹, Yu Tang, He-Jing Feng, Ji-Tian Liu, Richard P Hsung.

Abstract

A highly π-facial selective and regioselective fluorination of chiral enamides is described. The reaction involves an enantioselective fluorination exclusively at the electron-rich enamide olefin with N-F reagents such as Selectfluor and N-fluoro-benzenesulfonimide [NFSI] accompanied by trapping of the β-fluoro-iminium cationic intermediate with water. The resulting N,O-hemiacetal could be oxidized using Dess-Martin periodinane, leading to an asymmetric sequence for syntheses of chiral α-fluoro-imides and optically enriched α-fluoro-ketones.

Entities: Chemical Disease Gene

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Year: 2015 PMID： 25582419 PMCID： PMC4540344 DOI： 10.1021/ol503591d

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

37 in total

1. Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst.

Authors: Vivek Rauniyar; Aaron D Lackner; Gregory L Hamilton; F Dean Toste
Journal: Science Date: 2011-12-23 Impact factor: 47.728

Review 2. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors: Jun-An Ma; Dominique Cahard
Journal: Chem Rev Date: 2004-12 Impact factor: 60.622

3. A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors: Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal: Org Lett Date: 2007-10-02 Impact factor: 6.005

4. Stereoselective α-fluorination of N-acyloxazolidinones at room temperature within 1 h.

Authors: Joseph Alvarado; Aaron T Herrmann; Armen Zakarian
Journal: J Org Chem Date: 2014-06-20 Impact factor: 4.354

5. Attaching the fluorine atom to organic molecules using BrF3 and other reagents directly derived from F2.

Authors: Shlomo Rozen
Journal: Acc Chem Res Date: 2005-10 Impact factor: 22.384

Review 6. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors: Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal: Chem Rev Date: 2013-12-03 Impact factor: 60.622

7. Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors: John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal: Org Lett Date: 2009-08-20 Impact factor: 6.005

2. Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.

Authors: Toolika Agrawal; Robert T Martin; Stephen Collins; Zachary Wilhelm; Mytia D Edwards; Osvaldo Gutierrez; Joshua D Sieber
Journal: J Org Chem Date: 2021-03-16 Impact factor: 4.354

2 in total

A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.

1. Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst.

Review 2. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

3. A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

4. Stereoselective α-fluorination of N-acyloxazolidinones at room temperature within 1 h.

5. Attaching the fluorine atom to organic molecules using BrF3 and other reagents directly derived from F2.

Review 6. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

7. Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

8. Copper-catalyzed coupling of amides and carbamates with vinyl halides.

9. CuI/N,N-dimethylglycine-catalyzed coupling of vinyl halides with amides or carbamates.

10. Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2 + 2] cycloaddition cascade.

Review 1. Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine.

2. Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.