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 Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones.

Literature DB >> 28032765

Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones.

Ransheng Ding¹, Pegah R Bakhshi¹, Christian Wolf¹.

Abstract

An organocatalytic method that achieves insertion of isatins into aryl difluoronitromethyl ketones under mild conditions is described. The reaction occurs in the presence of 20 mol % of DBU and with 100% atom economy. A series of isatin derived difluoronitromethyl substituted tertiary alcohol benzoates and naphthoates were prepared in 81-99% yield. The general synthetic usefulness of these 3-hydroxyoxindole derivatives is demonstrated with the selective reduction to fluorooximes.

Entities: CellLine Chemical

Mesh：

Substances：
Ketones
Isatin

Year: 2017 PMID： 28032765 PMCID： PMC5294883 DOI： 10.1021/acs.joc.6b02704

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

23 in total

1. Asymmetric Alkylation of Nitroalkanes We thank the National Science Foundation and the National Institutes of Health (NIH), General Medical Sciences, for their generous support of our programs. Rhône-Poulenc graciously provided a postdoctoral fellowship for J.-P. S. Mass spectra were provided by the Mass Spectrometry Facility of the University of California, San Francisco, supported by the NIH Division of Research Resources.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-09-01 Impact factor: 15.336

2. Extension of the self-consistent spectrophotometric basicity scale in acetonitrile to a full span of 28 pKa units: unification of different basicity scales.

Authors: Ivari Kaljurand; Agnes Kütt; Lilli Sooväli; Toomas Rodima; Vahur Mäemets; Ivo Leito; Ilmar A Koppel
Journal: J Org Chem Date: 2005-02-04 Impact factor: 4.354

3. Asymmetric synthesis of chiral 1,3-diaminopropanols: bisoxazolidine-catalyzed C-C bond formation with α-keto amides.

Authors: Hanhui Xu; Christian Wolf
Journal: Angew Chem Int Ed Engl Date: 2011-10-31 Impact factor: 15.336

4. Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: toward the facile C-alkylation of nitroalkanes.

Authors: Peter G Gildner; Amber A S Gietter; Di Cui; Donald A Watson
Journal: J Am Chem Soc Date: 2012-06-12 Impact factor: 15.419

5. Asymmetric nitroaldol reaction catalyzed by a C2-symmetric bisoxazolidine ligand.

Authors: Shuanglong Liu; Christian Wolf
Journal: Org Lett Date: 2008-04-03 Impact factor: 6.005

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. Design and synthesis of novel fluoropeptidomimetics as potential mimics of the transition state during peptide hydrolysis.

Authors: Subhash C Annedi; Weiyong Li; Sheeba Samson; Lakshmi P Kotra
Journal: J Org Chem Date: 2003-02-07 Impact factor: 4.354

8. Metal-Free Reduction of Aromatic and Aliphatic Nitro Compounds to Amines: A HSiCl3-Mediated Reaction of Wide General Applicability.

Authors: M Orlandi; F Tosi; M Bonsignore; M Benaglia
Journal: Org Lett Date: 2015-08-11 Impact factor: 6.005

9. Catalytic insertion of aldehydes into dihalonitroacetophenones via sequential bond scission-aldol reaction-acyl transfer.

Authors: Ransheng Ding; Christian Wolf
Journal: Chem Commun (Camb) Date: 2016-02-05 Impact factor: 6.222

10. Enantioselective synthesis of 3-hydroxy oxindoles by ytterbium-catalysed decarboxylative addition of β-ketoacids to isatins.

Authors: Zhiqiang Duan; Jianlin Han; Ping Qian; Zirui Zhang; Yi Wang; Yi Pan
Journal: Org Biomol Chem Date: 2013-08-27 Impact factor: 3.876

6 in total

Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones.

2. Extension of the self-consistent spectrophotometric basicity scale in acetonitrile to a full span of 28 pKa units: unification of different basicity scales.

3. Asymmetric synthesis of chiral 1,3-diaminopropanols: bisoxazolidine-catalyzed C-C bond formation with α-keto amides.

4. Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: toward the facile C-alkylation of nitroalkanes.

5. Asymmetric nitroaldol reaction catalyzed by a C2-symmetric bisoxazolidine ligand.

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

7. Design and synthesis of novel fluoropeptidomimetics as potential mimics of the transition state during peptide hydrolysis.

8. Metal-Free Reduction of Aromatic and Aliphatic Nitro Compounds to Amines: A HSiCl3-Mediated Reaction of Wide General Applicability.

9. Catalytic insertion of aldehydes into dihalonitroacetophenones via sequential bond scission-aldol reaction-acyl transfer.

10. Enantioselective synthesis of 3-hydroxy oxindoles by ytterbium-catalysed decarboxylative addition of β-ketoacids to isatins.

1. Organocatalytic Stereoselective Synthesis of Fluorinated 3,3'-Linked Bisoxindoles.

2. Catalytic Asymmetric Allylic Amination with Isatins, Sulfonamides, Imides, Amines, and N-Heterocycles.

3. Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.

4. Enantioseparation and racemization of α-aryl-α-fluoroacetonitriles.

5. Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.

6. Chemodivergent Csp³─F bond functionalization and cross-electrophile alkyl-alkyl coupling with alkyl fluorides.