Catalytic enantioselective synthesis of carboxy-substituted 2-isoxazolines by cascade oxa-Michael-cyclization

Literature Information

Publication Date 2018-01-02
DOI 10.1039/C7OB02722B
Impact Factor 3.876
Authors

Hyo-Jun Lee, Bora Eun, Eonseon Sung, Gil Tae Hwang, Young Kwan Ko, Chang-Woo Cho


View Original

Abstract

An efficient quinidine-based phase-transfer-catalyzed enantioselective cascade oxa-Michael-cyclization reaction of hydroxylamine with various β-carboxy-substituted α,β-unsaturated ketones has been achieved for the preparation of chiral carboxy-substituted 2-isoxazolines. This cascade reaction provided the desired products in good yields (up to 98%) with excellent enantioselectivities (91–96% ee). In addition, the cascade reaction was effectively applied to the first catalytic asymmetric synthesis of the herbicide (S)-methiozolin.

Related Literature

Hydrogen bonding of water in 3-methylpyridine studied by O 1s X-ray emission and absorption spectroscopy

Koichiro Sadakane, Takashi Tokushima, Yasunori Senba, Haruhiko Ohashi

2011-12-06 Communication

DOI: 10.1039/C2CP23276F

Front cover

Cover

DOI: 10.1039/C2CP90002E

Optical effects of shadow masks on short circuit current of organic photovoltaic devices

Chi-Feng Lin, Bing-Hong Lin, Shun-Wei Liu, Wei-Feng Hsu, Mi Zhang, Tien-Lung Chiu, Mau-Kuo Wei, Jiun-Haw Lee

2012-02-10 Paper

DOI: 10.1039/C2CP00033D

Lyotropic liquid crystalline phase behaviour in amphiphile–protic ionic liquid systems

Tamar L. Greaves, Celesta Fong, Calum J. Drummond

2012-01-19 Paper

DOI: 10.1039/C2CP23698B

Sea urchin TiO2–nanoparticle hybrid composite photoelectrodes for CdS/CdSe/ZnS quantum-dot-sensitized solar cells

Eui-Hyun Kong, Yong-June Chang, Yoon-Cheol Park, Yeon-Hee Yoon, Hyun-Jin Park, Hyun Myung Jang

2012-02-08 Paper

DOI: 10.1039/C2CP24106D

Effect of doped zinc species on the photocatalytic activity of gallium oxide for hydrogen production

Katsuya Shimura, Hisao Yoshida

2011-12-20 Paper

DOI: 10.1039/C2CP23220K

Photophysics of indole-2-carboxylic acid in an aqueous environment studied by fluorescence spectroscopy in combination with ab initio calculations

Annemarie Huijser, Michał F. Rode, Alice Corani, Andrzej L. Sobolewski, Villy Sundström

2012-01-10 Paper

DOI: 10.1039/C2CP22958G

Proton magnetic resonance imaging with para-hydrogen induced polarization

Lisandro Buljubasich, Laura M. Schreiber, Hans W. Spiess, Kerstin Münnemann

2012-01-12 Paper

DOI: 10.1039/C2CP22822J

The interaction of His337 with the Mn4Ca cluster of photosystem II

Simon Petrie, Phillip Gatt, Robert Stranger, Ron J. Pace

2012-02-13 Paper

DOI: 10.1039/C2CP23935C

You might also like

Compound Q&A

What are the main uses of (3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8)?

(3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8) is primari...

79066-03-8(3.beta.)-3-Hydroxy-...
Compound Q&A

What regulatory guidelines apply to 5-(aminomethyl)-2-methoxyphenol (CAS: 89702-89-6)?

5-(Aminomethyl)-2-methoxyphenol (CAS: 89702-89-6) is classified under GHS as a s...

89702-89-65-(aminomethyl)-2-me...
Compound Q&A

What is Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7)?

Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7) is a heterocyclic organic compo...

28981-13-7Thieno[2,3-c]pyridin...
Compound Q&A

Is 1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride (CAS: 1185311-28-7) safe?

1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride is generally ...

1185311-28-71-[(6-Methoxy-3-pyri...
Compound Q&A

What regulatory guidelines apply to [(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2)?

[(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2) is regulated und...

146404-58-2[(2E)-3-Phenyl-2-pro...
Compound Q&A

What regulatory guidelines apply to 6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7)?

6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7) falls under the scope of the Glob...

1620515-86-76-Bromo-7-methoxyqui...
Compound Q&A

What industries use (2R)-1-(1-Benzofuran-2-yl)-N-propyl-2-pentanamine (CAS: 260550-89-8)?

This compound is primarily used in the pharmaceutical industry for the developme...

260550-89-8(2R)-1-(1-Benzofuran...
1228013-15-71-Ethyl-7-[2-methyl-...
Compound Q&A

Are there alternatives to {5-(Acryloylamino)-2-[(dimethylamino)methyl]phenyl}boronic acid (CAS: 1217500-78-1) in synthesis?

Alternative reagents such as 2-[(dimethylamino)methyl]phenylboronic acid or rela...

1217500-78-1{5-(Acryloylamino)-2...
Compound Q&A

What is 3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2)?

3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2) is an organic compound with the...

310881-48-23-(Piperidin-4-yloxy...

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.