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 | Year: 2012
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.
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 | Year: 2012
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.