Construction of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates

Literature Information

Publication Date 2018-11-19
DOI 10.1039/C8OB02748J
Impact Factor 3.876
Authors

Hou-Ze Gui, Yin Wei


View Original

Abstract

A useful and convenient strategy for the diastereoselective synthesis of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates was established. A diverse set of spirooxindole derivatives were synthesized in good to excellent yields and diastereoselectivities. Good enantioselectivities (up to 96 : 4 er) were obtained in the subsequent asymmetric study.

Related Literature

Exploration of significant influences of the operating conditions on the local O2 transport in proton exchange membrane fuel cells (PEMFCs)

Shuiyun Shen, Xiaojing Cheng, Chao Wang, Xiaohui Yan, Changchun Ke, Jiewei Yin, Junliang Zhang

2017-09-06 Paper

DOI: 10.1039/C7CP04837H

Langmuir–Blodgett films of perylene bisimide derivatives and fluorescent recognition of diamines

Congdi Shang, Li Wang, Yanqin An, Ping Chen, Xingmao Chang, Yanyu Qi, Rui Kang, Yu Fang

2017-08-14 Paper

DOI: 10.1039/C7CP04235C

Swelling of micro-hydrogels with a crosslinker gradient

Niels Boon, Peter Schurtenberger

2017-06-06 Paper

DOI: 10.1039/C7CP02434G

Light-induced piston nanoengines: ultrafast shuttling of a styryl dye inside cucurbit[7]uril

Ekaterina Y. Chernikova, Yuri V. Fedorov, Olga A. Fedorova, François Maurel, Gediminas Jonusauskas

2017-09-08 Communication

DOI: 10.1039/C7CP04283C

Unravelling hydrogen bonding interactions of tryptamine–water dimer from neutral to cation

Zongyuan Liu, Carl O. Trindle, Quanli Gu, Wei Wu, Peifeng Su

2017-08-04 Paper

DOI: 10.1039/C7CP03491A

Elucidating the mechanism of MgB2 initial hydrogenation via a combined experimental–theoretical study

Keith G. Ray, Leonard E. Klebanoff, Jonathan R. I. Lee, Vitalie Stavila, Tae Wook Heo, Patrick Shea, Alexander A. Baker, Shinyoung Kang, Michael Bagge-Hansen, Yi-Sheng Liu, James L. White, Brandon C. Wood

2017-07-19 Paper

DOI: 10.1039/C7CP03709K

Unveiling universal trends for the energy level alignment in organic/oxide interfaces

José I. Martínez, Fernando Flores, José Ortega, Sylvie Rangan, Charles M. Ruggieri, Robert A. Bartynski

2017-08-08 Perspective

DOI: 10.1039/C7CP03853D

Contents list

Front/Back Matter

DOI: 10.1039/C7CP90200J

Quercetin and its analogues: optical and acido–basic properties

David Biedermann, Kateřina Valentová, Vladimír Křen, Martin Kubala

2017-09-07 Paper

DOI: 10.1039/C7CP03845C

You might also like

Compound Q&A

What is 3-Fluoro-2-methylbenzylamine (CAS: 771573-36-5)?

3-Fluoro-2-methylbenzylamine is an organic compound with the CAS number 771573-3...

771573-36-53-Fluoro-2-methylben...
Compound Q&A

Is Tert-butyl 2-(oxetan-3-ylidene)acetate (CAS: 1207175-03-8) safe?

Tert-butyl 2-(oxetan-3-ylidene)acetate is considered safe for its intended uses ...

1207175-03-8Tert-butyl 2-(oxetan...
Compound Q&A

What precautions should be taken when handling 4-Acetyl-2-fluorobenzonitrile (CAS: 214760-18-6)?

Proper personal protective equipment (PPE) such as gloves, goggles, and a lab co...

214760-18-64-Acetyl-2-fluoroben...
Compound Q&A

How is 2-Ethyl-4-methyl-1,3-thiazole (CAS: 15679-12-6) typically synthesized?

2-Ethyl-4-methyl-1,3-thiazole is commonly synthesized via the reaction of thiour...

15679-12-62-Ethyl-4-methyl-1,3...
Compound Q&A

How should 5',5''-([2,2'-Bithiophene]-5,5'-diyl)bis(([1,1':3',1''-terphenyl]-4,4''-dicarboxylic acid)) (CAS: 1227780-71-3) be stored?

This compound should be stored in a cool, dry place away from direct sunlight an...

1227780-71-35',5''''-([2,2'-Bith...
Compound Q&A

What regulatory guidelines apply to L-Lysine Acetate Salt (CAS: 52315-92-1)?

L-Lysine Acetate Salt (CAS: 52315-92-1) is subject to various regulatory guideli...

52315-92-1L-LYSINE ACETATE SAL...
Compound Q&A

Is 6-Fluoro-3-hydroxy-2-pyrazinecarboxamide (CAS: 259793-96-9) safe?

6-Fluoro-3-hydroxy-2-pyrazinecarboxamide (CAS: 259793-96-9) is generally conside...

259793-96-96-Fluoro-3-hydroxy-2...
Compound Q&A

What are the physical and chemical properties of 1,1'-Sulfonylbis(1H-imidazole) (CAS: 7189-69-7)?

1,1'-Sulfonylbis(1H-imidazole) is a crystalline solid with a molecular weight of...

7189-69-71,1'-Sulfonylbis(1H-...
Compound Q&A

What industries use 4-methyl-7-nitro-1H-indole-3-carbonitrile (CAS: 289483-82-5)?

4-Methyl-7-nitro-1H-indole-3-carbonitrile (CAS: 289483-82-5) is primarily used i...

289483-82-54-methyl-7-nitro-1H-...
Compound Q&A

How should waste containing 5-Bromo-3-indolyl-beta-galactoside (CAS: 97753-82-7) be handled?

Waste containing 5-Bromo-3-indolyl-beta-galactoside (CAS: 97753-82-7) should be ...

97753-82-75-Bromo-3-indolyl-be...

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.