ChemInform Abstract: Practical Asymmetric Synthesis of (S)-MA20565, a Wide-Spectrum Agricultural Fungicide

Autor:	Jun Takehara, Ken Tanaka, Yasushi Shiga, Fumihiko Ohno, Manabu Katsurada, Miwa Miyagi, Kazuya Okano, Masatsugu Oda
Rok vydání:	2010
Předmět:	chemistry.chemical_compound Trifluoromethyl Hydroxylamine chemistry Methanesulfonyl chloride Yield (chemistry) Convergent synthesis Enantioselective synthesis chemistry.chemical_element General Medicine Transfer hydrogenation Medicinal chemistry Ruthenium
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200018164
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
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