Concise enantioselective synthesis of duloxetine via direct catalytic asymmetric aldol reaction of thioamide

Yuta Suzuki; Mitsutaka Iwata; Ryo Yazaki; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/jo300566p

Concise enantioselective synthesis of duloxetine via direct catalytic asymmetric aldol reaction of thioamide

Yuta Suzuki, Mitsutaka Iwata, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

研究成果: Article › 査読

30 被引用数 (Scopus)

抄録

Direct catalytic asymmetric aldol reaction of thioamide offers a new entry to the concise enantioselective synthesis of duloxetine. The direct aldol protocol was scalable (>20 g) to afford the aldol product in 92% ee after LiAlH ₄ reduction, and 84% of the chiral ligand was recovered after recrystallization. The following four steps of transformation delivered duloxetine.

本文言語	English
ページ（範囲）	4496-4500
ページ数	5
ジャーナル	Journal of Organic Chemistry
巻	77
号	9
DOI	https://doi.org/10.1021/jo300566p
出版ステータス	Published - 2012 5月 4
外部発表	はい

ASJC Scopus subject areas

有機化学

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10.1021/jo300566p

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abstract = "Direct catalytic asymmetric aldol reaction of thioamide offers a new entry to the concise enantioselective synthesis of duloxetine. The direct aldol protocol was scalable (>20 g) to afford the aldol product in 92% ee after LiAlH 4 reduction, and 84% of the chiral ligand was recovered after recrystallization. The following four steps of transformation delivered duloxetine.",

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AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

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AB - Direct catalytic asymmetric aldol reaction of thioamide offers a new entry to the concise enantioselective synthesis of duloxetine. The direct aldol protocol was scalable (>20 g) to afford the aldol product in 92% ee after LiAlH 4 reduction, and 84% of the chiral ligand was recovered after recrystallization. The following four steps of transformation delivered duloxetine.

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Concise enantioselective synthesis of duloxetine via direct catalytic asymmetric aldol reaction of thioamide

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