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Literature DB >> 26001406

Ligand-Enabled Stereoselective β-C(sp(3))-H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-amino Acids.

Ru-Yi Zhu¹, Keita Tanaka¹, Gen-Cheng Li¹, Jian He¹, Hai-Yan Fu¹, Su-Hua Li¹, Jin-Quan Yu¹.

Abstract

A quinoline-based ligand was shown to promote palladium-catalyzed β-C(sp(3))-H fluorination for the first time. A range of unnatural enantiopure fluorinated α-amino acids were obtained through sequential β-C(sp(3))-H arylation and subsequent stereoselective fluorination from readily available L-alanine.

Entities: Chemical Disease Species

Mesh：

Substances：
Amino Acids
Fluorine

Year: 2015 PMID： 26001406 PMCID： PMC4934178 DOI： 10.1021/jacs.5b04088

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

30 in total

1. Stereoselective synthesis of chiral α-amino-β-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp(3) )-H bonds.

Authors: Qi Zhang; Kai Chen; Weihao Rao; Yuejun Zhang; Fa-Jie Chen; Bing-Feng Shi
Journal: Angew Chem Int Ed Engl Date: 2013-10-31 Impact factor: 15.336

2. Palladium(II)-catalyzed selective monofluorination of benzoic acids using a practical auxiliary: a weak-coordination approach.

Authors: Kelvin S L Chan; Masayuki Wasa; Xisheng Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2011-07-11 Impact factor: 15.336

3. Biosynthetic alanine racemase of Salmonella typhimurium: purification and characterization of the enzyme encoded by the alr gene.

Authors: N Esaki; C T Walsh
Journal: Biochemistry Date: 1986-06-03 Impact factor: 3.162

4. Steric Crowding Makes Challenging C(sp3)-F Reductive Eliminations Feasible.

Authors: Shu-Bin Zhao; Jennifer J Becker; Michel R Gagné
Journal: Organometallics Date: 2011-08-08 Impact factor: 3.876

Review 5. Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Authors: Keary M Engle; Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2011-01-24 Impact factor: 15.336

Review 6. The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination.

Authors: Vladimir V Grushin
Journal: Acc Chem Res Date: 2010-01-19 Impact factor: 22.384

7. Competition between sp³-C-N vs sp³-C-F reductive elimination from Pd(IV) complexes.

Authors: Mónica H Pérez-Temprano; Joy M Racowski; Jeff W Kampf; Melanie S Sanford
Journal: J Am Chem Soc Date: 2014-02-28 Impact factor: 15.419

8. Pd(OAc)2-catalyzed regioselective aromatic C-H bond fluorination.

Authors: Shao-Jie Lou; Dan-Qian Xu; Ai-Bao Xia; Yi-Feng Wang; Yun-Kui Liu; Xiao-Hua Du; Zhen-Yuan Xu
Journal: Chem Commun (Camb) Date: 2013-07-14 Impact factor: 6.222

9. Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

Authors: Thanh Truong; Kristine Klimovica; Olafs Daugulis
Journal: J Am Chem Soc Date: 2013-06-12 Impact factor: 15.419

10. Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.

Authors: Ru-Yi Zhu; Jian He; Xiao-Chen Wang; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2014-09-15 Impact factor: 15.419

23 in total

1. Ligand-Enabled Arylation of γ-C-H Bonds.

Authors: Suhua Li; Ru-Yi Zhu; Kai-Jiong Xiao; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2016-02-25 Impact factor: 15.336

2. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors: Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal: Chem Rev Date: 2016-12-02 Impact factor: 60.622

3. Pd-Catalyzed γ-C(sp³)-H Fluorination of Free Amines.

Authors: Yan-Qiao Chen; Sukriti Singh; Yongwei Wu; Zhen Wang; Wei Hao; Pritha Verma; Jennifer X Qiao; Raghavan B Sunoj; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2020-05-18 Impact factor: 15.419

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors: John C K Chu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2017-12-05 Impact factor: 15.336

Ligand-Enabled Stereoselective β-C(sp(3))-H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-amino Acids.

1. Stereoselective synthesis of chiral α-amino-β-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp(3) )-H bonds.

2. Palladium(II)-catalyzed selective monofluorination of benzoic acids using a practical auxiliary: a weak-coordination approach.

3. Biosynthetic alanine racemase of Salmonella typhimurium: purification and characterization of the enzyme encoded by the alr gene.

4. Steric Crowding Makes Challenging C(sp3)-F Reductive Eliminations Feasible.

Review 5. Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Review 6. The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination.

7. Competition between sp³-C-N vs sp³-C-F reductive elimination from Pd(IV) complexes.

8. Pd(OAc)2-catalyzed regioselective aromatic C-H bond fluorination.

9. Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

10. Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.

1. Ligand-Enabled Arylation of γ-C-H Bonds.

2. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

3. Pd-Catalyzed γ-C(sp³)-H Fluorination of Free Amines.

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

5. Highly Versatile β-C(sp³)-H Iodination of Ketones Using a Practical Auxiliary.

6. Total Synthesis and Stereochemical Assignment of Streptide.

7. Distal γ-C(sp³ )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

8. An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary.

9. Ligand-Enabled β-C(sp³)-H Olefination of Free Carboxylic Acids.

10. Ligand-Promoted C(sp(3) )-H Olefination en Route to Multi-functionalized Pyrazoles.

Review 5. Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Review 6. The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination.

Review 4. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.