Practical Asymmetric Synthesis of (S)-MA20565, a Wide-Spectrum Agricultural Fungicide
| Autor: | Yasushi Shiga, Kazuya Okano, Manabu Katsurada, Jun Takehara, Fumihiko Ohno, Ken Tanaka, Miwa Miyagi, Masatsugu Oda |
|---|---|
| Rok vydání: | 1999 |
| Předmět: |
Magnetic Resonance Spectroscopy
Trifluoromethyl Spectrophotometry Infrared Methanesulfonyl chloride Stereochemistry Organic Chemistry Convergent synthesis Enantioselective synthesis chemistry.chemical_element Transfer hydrogenation Amides Medicinal chemistry Fungicides Industrial Ruthenium chemistry.chemical_compound Hydroxylamine chemistry Yield (chemistry) Acetamides Imines Amines |
| Zdroj: | The Journal of Organic Chemistry. 65:432-437 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo991271z |
| Popis: | A practical asymmetric synthesis of a wide-spectrum agricultural fungicide, (S)-MA20565 (1), is described. The convergent synthesis was achieved starting from commercially available 3-(trifluoromethyl)aniline (7) in 44% overall yield through five steps and 2-bromobenzaldehyde (9) in 48% overall yield through four steps, respectively. (S)-O-[1-(3-Trifluoromethylphenyl)ethyl]hydroxylamine (2), a key intermediate of 1, was prepared via ruthenium(II)-catalyzed asymmetric transfer hydrogenation of 1-(3-trifluoromethylphenyl)ethanone (6) followed by chlorination using methanesulfonyl chloride and oxyamination using potassium acetohydroxamate with high level of stereocontrol. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|