Concise Enantioselective Synthesis of Duloxetine via Direct Catalytic Asymmetric Aldol Reaction of Thioamide

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 LiAlH4 reduction, and 84% of the chiral ligand was recovered after recryst...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-05, Vol.77 (9), p.4496-4500
Main Authors: Suzuki, Yuta, Iwata, Mitsutaka, Yazaki, Ryo, Kumagai, Naoya, Shibasaki, Masakatsu
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Crystallization
Duloxetine Hydrochloride
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Ligands
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
Thioamides - chemistry
Thiophenes - chemical synthesis
Thiophenes - chemistry
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Summary: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 LiAlH4 reduction, and 84% of the chiral ligand was recovered after recrystallization. The following four steps of transformation delivered duloxetine.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300566p