An improved lanthanum catalyst system for asymmetric amination: Toward a practical asymmetric synthesis of AS-3201 (ranirestat)

Tomoyuki Mashiko, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

61 Citations (Scopus)

Abstract

(Chemical Equation Presented) A catalytic asymmetric amination with a lanthanum/amide complex was significantly improved. The use of lanthanum nitrate hydrate in place of lanthanum triisopropoxide made the process reproducible, scalable, and cost-effective. The development of a ternary catalytic system of La/ligand/amine was a key to high ee and catalytic turnover. A 100 g scale reaction was performed to showcase a practical synthesis of a key intermediate for AS-3201, a highly potent aldose reductase inhibitor.

Original languageEnglish
Pages (from-to)2725-2728
Number of pages4
JournalOrganic Letters
Volume10
Issue number13
DOIs
Publication statusPublished - 2008
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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