- Practical Asymmetric Synthesis of (S)-MA20565, a Wide-Spectrum Agricultural Fungicide
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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.
- Tanaka, Ken,Katsurada, Manabu,Ohno, Fumihiko,Shiga, Yasushi,Oda, Masatsugu,Miyagi, Miwa,Takehara, Jun,Okano, Kazuya
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p. 432 - 437
(2007/10/03)
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- OPTICALLY ACTIVE METHOXYIMINOACETAMIDE DERIVATIVES, PROCESS FOR THE PREPARATION OF THEM, INTERMEDIATES THEREFOR, AND PESTICIDES CONTAINING THEM AS THE ACTIVE INGREDIENT
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An optically active methoxyiminoacetamide derivative represented by the following general formula (I) (in the above general formula, Ar represents an aryl group or a heteroaryl group, Y represents a hydrogen atom, a halogen atom, a C1-C4alkyl group, a C1-C4haloalkyl group, a C1-C4alkoxy group, a C1-C4haloalkoxy group, a C1-C4alkylthio group, a C2-C6alkynyloxy group, a cyano group, a nitro group or an aryl group and n is an integer of 1 to 3), wherein its angle of rotation shows a negative value in chloroform has markedly excellent activities as agricultural chemicals.
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