Bifunctional squaramide catalyzed stereoselective Mannich reaction of α-azido ketones with isatin-derived ketimines

Literature Information

Publication Date 2019-12-11
DOI 10.1039/C9OB02208B
Impact Factor 3.876
Authors

Seda Karahan, Cihangir Tanyeli


View Original

Abstract

Asymmetric organocatalytic Mannich reaction of α-azido ketones and N-Boc protected isatin-derived ketimines were investigated for the first time. Examination of both 2-adamantyl and 3,5-bis(trifluoromethyl)aniline substituted quinine-based squaramides afforded chiral Mannich bases with two contiguous stereogenic centers in high yields (up to 97%) and stereoselectivity (up to dr = 24 : 1 syn : anti and 96% ee). Azido and masked amino functionalities of the potent heterocycle precursor adducts were utilized in representative examples.

Related Literature

Recent progress of MXene as an energy storage material

Yuqiang Wu, Mengtao Sun

2024-01-05 Minireview

DOI: 10.1039/D3NH00402C

siRNA-loaded DNA nanostructures restore endothelial leakiness

Arun Richard Chandrasekaran

2023-10-04 Editorial

DOI: 10.1039/D3NH90040A

Polyurethane-based nanocomposite film with thermal deicing capability and anti-erosion for wind turbine blades protection in extreme environments

Xiaofeng Cui, Na Zhang, Ming Huang, Guoli Gao, Shihai Liu, Chuntai Liu

2023-10-14 Paper

DOI: 10.1039/D3TA05595G

Tumor microenvironment-responsive degradable silica nanoparticles: design principles and precision theranostic applications

Kaiyuan Tang, Zilu Liu, Zhijing Zhang, Shufan Duan, Hui Wang, Hui Yang, Dongliang Yang, Wenpei Fan

2023-11-29 Review Article

DOI: 10.1039/D3NH00388D

Simple phenylpropanoids: recent advances in biological activities, biosynthetic pathways, and microbial production

Zhanpin Zhu, Ruibing Chen

2023-10-09 Review Article

DOI: 10.1039/D3NP00012E

Electrifying H2O2 synthesis with g-C3N4-based single atom catalysts

Jungki Ryu

2023-10-04 Editorial

DOI: 10.1039/D3NH90041J

NIR-activated quercetin-based nanogels embedded with CuS nanoclusters for the treatment of drug-resistant biofilms and accelerated chronic wound healing

Amit Nain, Yu-Ting Tseng, Akash Gupta, Yu-Feng Lin, Sangili Arumugam, Yu-Fen Huang

2023-09-19 Communication

DOI: 10.1039/D3NH00275F

Contents list

2023-12-18 Front/Back Matter

DOI: 10.1039/D4NH90002B

Pneumatic nano-sieve for CRISPR-based detection of drug-resistant bacteria

Ruonan Peng, Fengjun Xu, Richard Hailstone, Yujie Men, Ke Du

2023-10-18 Communication

DOI: 10.1039/D3NH00365E

Coke relocation and Mo immobilization in donut-shaped Mo/HZSM-5 catalysts for methane dehydroaromatization

Ming Cheng, Hugo Cruchade, Ludovic Pinard, Eddy Dib, Honghai Liu, Jiujiang Wang, Xinmei Liu, Zi-Feng Yan, Zhengxing Qin, Svetlana Mintova

2023-11-10 Paper

DOI: 10.1039/D3TA05418G

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.