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Literature DB >> 29608314

Stereoselective Synthesis of Optically Pure 2-Amino-2'-hydroxy-1,1'-binaphthyls.

Hagit Forkosh¹, Vlada Vershinin¹, Hagai Reiss¹, Doron Pappo¹.

Abstract

Direct entry to optically pure 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) derivatives by an iron-catalyzed stereoselective oxidative cross-coupling reaction between 2-naphthol and 2-aminonaphthalene with a labile chiral auxiliary is reported. This efficient method offers entry to tailor-designed ( R a)- and ( S a)-NOBINs that are not accessible by any other means.

Entities: Chemical

Year: 2018 PMID： 29608314 DOI： 10.1021/acs.orglett.8b00800

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

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Cited

7 in total

1. Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors: Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal: J Am Chem Soc Date: 2018-04-25 Impact factor: 15.419

2. Catalytic Oxidative Coupling of Phenols and Related Compounds.

Authors: Jingze Wu; Marisa C Kozlowski
Journal: ACS Catal Date: 2022-05-18 Impact factor: 13.700

3. Aerobic Catalyzed Oxidative Cross-Coupling of N,N-Disubstituted Anilines and Aminonaphthalenes with Phenols and Naphthols.

Authors: Thomas J Paniak; Marisa C Kozlowski
Journal: Org Lett Date: 2020-02-12 Impact factor: 6.005

Stereoselective Synthesis of Optically Pure 2-Amino-2'-hydroxy-1,1'-binaphthyls.

1. Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

2. Catalytic Oxidative Coupling of Phenols and Related Compounds.

3. Aerobic Catalyzed Oxidative Cross-Coupling of N,N-Disubstituted Anilines and Aminonaphthalenes with Phenols and Naphthols.

Review 4. Synthetic Applications of Oxidative Aromatic Coupling-From Biphenols to Nanographenes.

5. Mechanistic Insights into the FeCl₃-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes.

6. Conformational enantiodiscrimination for asymmetric construction of atropisomers.

Review 7. Recent Advances in Asymmetric Iron Catalysis.

Stereoselective Synthesis of Optically Pure 2-Amino-2'-hydroxy-1,1'-binaphthyls.

1. Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

2. Catalytic Oxidative Coupling of Phenols and Related Compounds.

3. Aerobic Catalyzed Oxidative Cross-Coupling of N,N-Disubstituted Anilines and Aminonaphthalenes with Phenols and Naphthols.

Review 4. Synthetic Applications of Oxidative Aromatic Coupling-From Biphenols to Nanographenes.

5. Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes.

6. Conformational enantiodiscrimination for asymmetric construction of atropisomers.

Review 7. Recent Advances in Asymmetric Iron Catalysis.

5. Mechanistic Insights into the FeCl₃-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes.