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Literature DB >> 25414091

Asymmetric dearomatization of β-naphthols through an amination reaction catalyzed by a chiral phosphoric acid.

Shou-Guo Wang¹, Qin Yin, Chun-Xiang Zhuo, Shu-Li You.

Abstract

A highly efficient catalytic asymmetric dearomatization of naphthols by means of an electrophilic amination reaction catalyzed by chiral phosphoric acid is presented. This protocol provides a facile access to functionalized β-naphthalenone compounds with a chiral quaternary carbon center in excellent yields and enantioselectivity (up to 99% yield, up to 96% ee).

Entities: Chemical

Keywords: amination reaction; asymmetric catalysis; dearomatization; naphthol; organocatalysis

Year: 2014 PMID： 25414091 DOI： 10.1002/anie.201409756

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

13 in total

1. Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization.

Authors: Christopher J Huck; David Sarlah
Journal: Chem Date: 2020-07-01 Impact factor: 22.804

2. A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

Authors: Dillon H Miles; Joan Guasch; F Dean Toste
Journal: J Am Chem Soc Date: 2015-06-12 Impact factor: 15.419

3. Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents.

Authors: Conghui Tang; Mikiko Okumura; Yunbo Zhu; Annie R Hooper; Yu Zhou; Yu-Hsuan Lee; David Sarlah
Journal: Angew Chem Int Ed Engl Date: 2019-06-24 Impact factor: 15.336

4. Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid.

Authors: Xiaoyu Yang; F Dean Toste
Journal: J Am Chem Soc Date: 2015-02-26 Impact factor: 15.419

5. An efficient nickel/silver co-catalyzed remote C-H amination of 8-aminoquinolines with azodicarboxylates at room temperature.

Authors: Ruinan Zhao; Yaocheng Yang; Xia Wang; Peng Ren; Qian Zhang; Dong Li
Journal: RSC Adv Date: 2018-11-05 Impact factor: 4.036

Asymmetric dearomatization of β-naphthols through an amination reaction catalyzed by a chiral phosphoric acid.

1. Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization.

2. A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

3. Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents.

4. Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid.

5. An efficient nickel/silver co-catalyzed remote C-H amination of 8-aminoquinolines with azodicarboxylates at room temperature.

6. Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction.

7. Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.

8. A Simple and Broadly Applicable C-N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents.

9. Organocatalytic asymmetric chlorinative dearomatization of naphthols.

10. A bio-inspired synthesis of oxindoles by catalytic aerobic dual C-H functionalization of phenols.