Regioselective catalytic asymmetric N-alkylation of isoxazol-5-ones with para-quinone methides

Literature Information

Publication Date 2020-03-14
DOI 10.1039/D0OB00393J
Impact Factor 3.876
Authors

Suo-Suo Qi, Zhen-Hui Jiang, Ming-Ming Chu, Yi-Feng Wang, Xue-Yang Chen, Wan-Zhen Ju, Dan-Qian Xu


View Original

Abstract

A highly regioselective and enantioselective N-alkylation of isoxazol-5-ones with para-quinone methides promoted by bi-functional squaramide catalysts was developed. This unexpected asymmetric N-addition of isoxazolinones afforded a series of enantioenriched N-diarylmethane substituted isoxazolinones with high yields and enantioselectivities (up to 97 : 3 er). This reaction not only provides a useful approach for intermolecular chiral C–N bond formation but also demonstrates the immense potential of isoxazol-5-ones as N-nucleophiles in catalytic asymmetric reactions.

Related Literature

Front cover

2023-11-20 Cover

DOI: 10.1039/D3NH90055J

Recent progress of MXene as an energy storage material

Yuqiang Wu, Mengtao Sun

2024-01-05 Minireview

DOI: 10.1039/D3NH00402C

A functional electrolyte containing propyl 4-methylbenzene sulfonate (PMBS) additive to improve the cycling performance of the LiNi0.8Co0.1Mn0.1O2/graphite full cell under the low temperature of −10 °C

Haijia Li, Jian Cai, Jianping Liao, Yiting Li, Xueyi Zeng, Xin He, Chaojun Fan, Zhen Ma, Junmin Nan

2023-11-10 Paper

DOI: 10.1039/D3TA04535H

A bio-inspired multifunctional interface layer for high performance zinc-ion batteries via novel in situ electropolymerization

Jun Wang, Xiuyang Zou, Lina Song, Jianguo Lu, Xiang Gao, Qinggang He

2023-10-04 Paper

DOI: 10.1039/D3TA04886A

Contact engineering for 2D Janus MoSSe/metal junctions

Yu Shu, Ting Li, Naihua Miao, Jian Gou, Xiaochun Huang, Zhou Cui, Rui Xiong, Cuilian Wen, Jian Zhou, Baisheng Sa, Zhimei Sun

2023-11-16 Communication

DOI: 10.1039/D3NH00450C

Dual carbon engineering enabling 1T/2H MoS2 with ultrastable potassium ion storage performance

Rong Hu, Yanqi Tong, Jinling Yin, Junxiong Wu, Jing Zhao, Dianxue Cao, Guiling Wang, Kai Zhu

2023-12-20 Communication

DOI: 10.1039/D3NH00404J

Microfluidic synthesis of nanomaterials for biomedical applications

2023-09-05 Review Article

DOI: 10.1039/D3NH00217A

SiO2 supported Ce–Co mixed oxide catalyzed selective allylic oxidation of cyclohexene

Aratikumari Suresh Prasad

2023-12-20 Paper

DOI: 10.1039/D3NJ04852G

2D-Ti3C2Tx MXene-supported Cu2S nanoflakes for supercapacitors and electrocatalytic oxygen evolution reaction

Debika Gogoi, Rajeshvari Samatbhai Karmur, Narendra Nath Ghosh

2023-10-25 Paper

DOI: 10.1039/D3TA05104H

You might also like

Compound Q&A

What regulatory guidelines apply to 6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1)?

6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1) falls under various...

1111638-05-16-Bromo-2-methylimid...
Compound Q&A

Are there alternatives to 1-Pyrrolidineethanol, β-methyl-α-phenyl-, (αS,βR) (CAS: 123620-80-4) in synthesis?

While there are no direct alternatives, similar compounds like 1-Pyrrolidineetha...

123620-80-41-Pyrrolidineethanol...
Compound Q&A

Is 4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) safe?

4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) is ...

1918-11-24-Methyl-2,6-bis(2-m...
Compound Q&A

How should 2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) be stored?

2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) should be stored in a...

77771-04-12-(3-Bromo-4-fluorop...
Compound Q&A

What are the physical and chemical properties of 4,5,6,7-Tetrahydro-1H-indazole hydrochloride (CAS: 18161-11-0)?

4,5,6,7-Tetrahydro-1H-indazole hydrochloride is a white crystalline solid with a...

18161-11-04,5,6,7-Tetrahydro-1...
Compound Q&A

What is (2R)-1-Methoxy-3-phenyl-2-propanamine (CAS: 59919-07-2)?

(2R)-1-Methoxy-3-phenyl-2-propanamine is a chiral organic compound with the CAS ...

59919-07-2(2R)-1-Methoxy-3-phe...
Compound Q&A

What industries use Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate (CAS: 56649-47-9)?

Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate is used in various industries...

56649-47-9Ethyl 1-(1-phenyleth...
Compound Q&A

What regulatory guidelines apply to 4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3)?

4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3) falls...

17676-24-34-[(1E,3S)-1-(4-Hydr...
Compound Q&A

What industries use (S)-3-Amino-5-phenylpentanoic acid hydrochloride (CAS: 331846-97-0)?

(S)-3-Amino-5-phenylpentanoic acid hydrochloride is primarily used in the pharma...

331846-97-0(S)-3-Amino-5-phenyl...
Compound Q&A

How is 7-methoxy-1-benzothiophene-2-carboxylic acid (CAS: 88791-07-5) typically synthesized?

7-Methoxy-1-benzothiophene-2-carboxylic acid is typically synthesized by reactin...

88791-07-57-methoxy-1-benzothi...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.