Practical asymmetric synthesis of β-hydroxy-β-trifluoromethylated ketonesvia the first example of the in situ generation of trifluoro-acetaldehyde and its successive asymmetric carbon–carbon bond formation reaction with chiral imines

Literature Information

Publication Date 2004-08-13
DOI 10.1039/B408226E
Impact Factor 6.222
Authors

Kazumasa Funabiki, Wataru Hashimoto, Masaki Matsui


View Original

Abstract

Not only trifluoroactaldehyde ethyl hemiacetal or hydrate but also other polyfluoroalkylaldehydes acetals or hydrates react with an equimolar amount of various chiral imines, followed by hydrolysis to produce the corresponding (S)-β-hydroxy-β-polyfluoroalkyl ketones in good yields with good enantioselectivities; furthermore, the ee of the products can be improved by simple recrystallization.

Related Literature

Brushed polyethylene glycol and phosphorylcholine for grafting nanoparticles against protein binding

Bo Wang, Thomas Blin, Aleksandr Käkinen, Xinwei Ge, Emily H. Pilkington, John F. Quinn, Michael R. Whittaker, Pu Chun Ke, Feng Ding

2016-09-23 Communication

DOI: 10.1039/C6PY01480A

Pyridine type zwitterionic polyurethane with both multi-shape memory effect and moisture-sensitive shape memory effect for smart biomedical application

Shaojun Chen, Zhankui Mei, Huanhuan Ren, Haitao Zhuo, Jianhong Liu, Zaochuan Ge

2016-07-26 Paper

DOI: 10.1039/C6PY01099G

ε-Methacryloyl-l-lysine based polypeptides and their thiol–ene click functionalization

Chunsheng Xiao, Shuangjiang Yu, Xuesi Chen

2014-12-18 Paper

DOI: 10.1039/C4PY01523A

Contents list

Front/Back Matter

DOI: 10.1039/C5PY90036K

Polymeric carbon Lewis base–acid adducts: poly(NHC–C60)

Miao Hong, Eugene Y.-X. Chen

2015-01-02 Paper

DOI: 10.1039/C4PY01488J

Amino-functionalized poly(N-vinylcaprolactam) derived from lysine: a sustainable polymer with thermo and pH dual stimuli response

Xiaojie Zhang, Chunsheng Xiao, Youhua Tao, Xianhong Wang

2016-10-26 Paper

DOI: 10.1039/C6PY01487A

Synthesis of hyperbranched polymers and their applications in analytical chemistry

Xiayu Peng

2014-12-04 Minireview

DOI: 10.1039/C4PY01462F

Ligand effects on cooperative supramolecular polymerization of platinum(ii) acetylide complexes

Zhao Gao, Junlong Zhu, Yifei Han, Xiaoqin Lv, Xiaolong Zhang, Feng Wang

2016-08-31 Communication

DOI: 10.1039/C6PY01440B

You might also like

Compound Q&A

What is 1-(2,4,6-Trifluorophenyl)ethanol (CAS: 1250113-83-7)?

1-(2,4,6-Trifluorophenyl)ethanol is an organic compound with the CAS number 1250...

1250113-83-71-(2,4,6-Trifluoroph...
Compound Q&A

Is 1-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-2-pyrrolidinone (CAS: 919111-34-5) safe?

1-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-2-pyrrolidinone (CAS: 919111-34-5) is ...

919111-34-51-(2,4-Dimethoxybenz...
Compound Q&A

What are the physical and chemical properties of (7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one (CAS: 51419-51-3)?

(7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one is a crystal...

51419-51-3(7S,15R)-6β,15-Diace...
Compound Q&A

What regulatory guidelines apply to rac-ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate, trans (CAS: 3618-04-0)?

The compound rac-ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate, trans (CAS: 3...

3618-04-0rac-ethyl (1r,4r)-4-...
Compound Q&A

What is the market or research trend for 2-(2,4-Difluorophenoxy)-3-nitropyridine (CAS: 175135-62-3)?

The market for 2-(2,4-Difluorophenoxy)-3-nitropyridine (CAS: 175135-62-3) is cur...

175135-62-32-(2,4-Difluoropheno...
Compound Q&A

What are the main uses of 6-Diazo-5-oxo-L-norleucine (CAS: 157-03-9)?

The main uses of 6-Diazo-5-oxo-L-norleucine (CAS: 157-03-9) include research in ...

157-03-96-Diazo-5-oxo-L-norl...
Compound Q&A

What precautions should be taken when handling 2-Aminoethyl-mono-amide-DOTA-tris(tBu ester) (CAS: 173308-19-5)?

When handling 2-Aminoethyl-mono-amide-DOTA-tris(tBu ester) (CAS: 173308-19-5), i...

173308-19-52-Aminoethyl-mono-am...
Compound Q&A

How is 5-Methylimidazo[1,2-a]pyridine-3-carbaldehyde (CAS: 178488-37-4) typically synthesized?

5-Methylimidazo[1,2-a]pyridine-3-carbaldehyde (CAS: 178488-37-4) can be synthesi...

178488-37-45-Methylimidazo[1,2-...
Compound Q&A

Are there alternatives to 2,4,6-Trihydroxyisophthalaldehyde (CAS: 4396-13-8) in synthesis?

There are alternative reagents that can be used in the synthesis of 2,4,6-Trihyd...

4396-13-82,4,6-Trihydroxyisop...
Compound Q&A

What is (2Z)-3-(5-Fluoro-1H-indol-3-yl)-2-sulfanylacrylic acid (CAS: 179461-52-0)?

(2Z)-3-(5-Fluoro-1H-indol-3-yl)-2-sulfanylacrylic acid is a chemical compound wi...

179461-52-0(2Z)-3-(5-Fluoro-1H-...

Source Journal

Chemical Communications

Chemical Communications
CiteScore: 8.6
Self-citation Rate: 4.7%
Articles per Year: 2458

ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry

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.