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Iridium-catalyzed enantioselective synthesis of chiral γ-amino alcohols and intermediates of (S)-duloxetine, (R)-fluoxetine, and (R)-atomoxetine

Chemistry

Iridium-catalyzed enantioselective synthesis of chiral γ-amino alcohols and intermediates of (S)-duloxetine, (R)-fluoxetine, and (R)-atomoxetine

C. Liu, L. Zhang, et al.

Discover how researchers Chengyu Liu and colleagues have designed innovative tridentate ferrocene-based phosphine ligands that enable iridium-catalyzed asymmetric hydrogenation of β-amino ketones, creating a pathway for the industrial production of valuable chiral γ-amino alcohols, including (S)-duloxetine and (R)-fluoxetine.

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Playback language: English
Abstract
Chiral γ-amino alcohols are prevalent structural motifs in pharmaceuticals. This paper details the design, synthesis, and evaluation of tridentate ferrocene-based phosphine ligands for iridium-catalyzed asymmetric hydrogenation of β-amino ketones, yielding diverse chiral γ-amino alcohols with high yields and enantioselectivities. Gram-scale reactions demonstrate the potential for industrial synthesis of chiral drugs like (S)-duloxetine, (R)-fluoxetine, and (R)-atomoxetine.
Publisher
Communications Chemistry
Published On
May 19, 2022
Authors
Chengyu Liu, Lei Zhang, Liming Cao, Yan Xiong, Yueyue Ma, Ruihua Cheng, Jinxing Ye
Tags
chiral γ-amino alcohols
phosphine ligands
asymmetric hydrogenation
β-amino ketones
iridium catalysis
pharmaceuticals
industrial synthesis

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