Concise enantioselective synthesis of duloxetine via direct catalytic asymmetric aldol reaction of thioamide

Yuta Suzuki, Mitsutaka Iwata, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticle

26 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4496-4500
Number of pages5
JournalJournal of Organic Chemistry
Volume77
Issue number9
DOIs
Publication statusPublished - May 4 2012

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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