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

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4496-4500
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	77
Issue number	9
DOIs	https://doi.org/10.1021/jo300566p
Publication status	Published - May 4 2012
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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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.",

author = "Yuta Suzuki and Mitsutaka Iwata and Ryo Yazaki and Naoya Kumagai and Masakatsu Shibasaki",

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AU - Suzuki, Yuta

AU - Iwata, Mitsutaka

AU - Yazaki, Ryo

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2012/5/4

Y1 - 2012/5/4

N2 - 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.

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

Abstract

All Science Journal Classification (ASJC) codes

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