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Literature DB >> 35007090

Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation.

Hyung Yoon¹, Alexandra Galls¹, Soren D Rozema¹, Scott J Miller¹.

Abstract

Enantioselective Cu-catalyzed C-O cross coupling reactions yielding atropisomeric resorcinol-bearing quinazolinones have been developed. Utilizing a new guanidinylated dimeric peptidic ligand, a set of products were generated in good yields with excellent stereocontrol. The transformation was readily scalable, and a range of product derivatizations were performed.

Entities: Chemical

Mesh：
Quinazolinones

Substances：
Quinazolinones

Year: 2022 PMID： 35007090 PMCID： PMC8968294 DOI： 10.1021/acs.orglett.1c04266

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

48 in total

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors: Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

2. Palladium-Catalyzed Atroposelective Coupling-Cyclization of 2-Isocyanobenzamides to Construct Axially Chiral 2-Aryl- and 2,3-Diarylquinazolinones.

Authors: Fan Teng; Ting Yu; Yan Peng; Weiming Hu; Huaanzi Hu; Yimiao He; Shuang Luo; Qiang Zhu
Journal: J Am Chem Soc Date: 2021-02-09 Impact factor: 15.419

3. Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings.

Authors: Yuntong Zhai; Xiaofei Chen; Wei Zhou; Mengyang Fan; Yisheng Lai; Dawei Ma
Journal: J Org Chem Date: 2017-04-26 Impact factor: 4.354

Review 4. Recent encounters with atropisomerism in drug discovery.

Authors: Peter W Glunz
Journal: Bioorg Med Chem Lett Date: 2017-12-06 Impact factor: 2.823

Review 5. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors: Christopher R Shugrue; Scott J Miller
Journal: Chem Rev Date: 2017-06-05 Impact factor: 60.622

6. A beta-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions.

Authors: Xin Lv; Weiliang Bao
Journal: J Org Chem Date: 2007-04-14 Impact factor: 4.354

7. Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization.

Authors: Motohiro Hirai; Shumpei Terada; Hiroaki Yoshida; Kenki Ebine; Tomoaki Hirata; Osamu Kitagawa
Journal: Org Lett Date: 2016-10-26 Impact factor: 6.005

Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation.

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

2. Palladium-Catalyzed Atroposelective Coupling-Cyclization of 2-Isocyanobenzamides to Construct Axially Chiral 2-Aryl- and 2,3-Diarylquinazolinones.

3. Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings.

Review 4. Recent encounters with atropisomerism in drug discovery.

Review 5. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

6. A beta-keto ester as a novel, efficient, and versatile ligand for copper(I)-catalyzed C-N, C-O, and C-S coupling reactions.

7. Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization.

8. Late-Stage Diversification: A Motivating Force in Organic Synthesis.

9. Late-stage oxidative C(sp³)-H methylation.

10. Site-Selective, Copper-Mediated O-Arylation of Carbohydrate Derivatives.

1. A Bifurcated Multicomponent Synthesis Approach to Polycyclic Quinazolinones.