title: Practical asymmetric synthesis of (S)-MA20565, a wide-spectrum agricultural fungicide.
abstract: 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.
authors.affiliation: Tsukuba Research Center, Mitsubishi Chemical Corporation, 8-3-1 Chuo, Ami, Inashiki, Ibaragi 300-0332, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Tanaka
authors.forename: M
authors.initials: M
authors.lastname: Katsurada
authors.forename: F
authors.initials: F
authors.lastname: Ohno
authors.forename: Y
authors.initials: Y
authors.lastname: Shiga
authors.forename: M
authors.initials: M
authors.lastname: Oda
authors.forename: M
authors.initials: M
authors.lastname: Miyagi
authors.forename: J
authors.initials: J
authors.lastname: Takehara
authors.forename: K
authors.initials: K
authors.lastname: Okano
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared
chemical_list: D000081:Acetamides; D000577:Amides; D000588:Amines; D005659:Fungicides, Industrial; D007097:Imines; C414084:MA 20565