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Suzuki Y.,Institute of Microbial Chemistry Tokyo | Suzuki Y.,University of Tokyo | Iwata M.,Institute of Microbial Chemistry Tokyo | Yazaki R.,University of Tokyo | And 2 more authors.
Journal of Organic Chemistry

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. © 2012 American Chemical Society. Source

Ogawa T.,Institute of Microbial Chemistry Tokyo | Kumagai N.,Institute of Microbial Chemistry Tokyo | Shibasaki M.,Institute of Microbial Chemistry Tokyo
Angewandte Chemie - International Edition

Softly does it: The title reaction proceeded under proton transfer conditions with a catalyst prepared from commercially available reagents to afford the desired product in high enantioselectivity. The reaction was compatible with a free amino group, thus allowing for expeditious access to enantiomerically enriched 1,5-benzothiazepines, which are important chemical entities in medicinal chemistry. Source

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