title: Concise enantioselective synthesis of duloxetine via direct catalytic asymmetric aldol reaction of thioamide.
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.
authors.affiliation: Institute of Microbial Chemistry, Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Suzuki
authors.forename: Mitsutaka
authors.initials: M
authors.lastname: Iwata
authors.forename: Ryo
authors.initials: R
authors.lastname: Yazaki
authors.forename: Naoya
authors.initials: N
authors.lastname: Kumagai
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D002384:Catalysis; D003460:Crystallization; D000068736:Duloxetine Hydrochloride; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D013854:Thioamides / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D008024:Ligands; D013854:Thioamides; D013876:Thiophenes; D000068736:Duloxetine Hydrochloride