Catalytic enantioselective synthesis of key intermediates for triazole antifungal agents

Masato Suzuki, Nobuki Kato, Motomu Kanaki, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

52 Citations (Scopus)

Abstract

(Chemical Equation Presented) A short-step synthesis of versatile chiral building blocks for triazole antifungal agents such as ZD0870 and Sch45450 was developed via catalytic enantioselective cyanosilylation of electron-deficient ketones as the key step. High enantioselectivity was produced using a catalyst prepared from Gd(HMDS)3 and ligand 5 in a 2:3 ratio. This new catalyst preparation method was superior to the previous method using Gd(O iPr)3 as a metal source. A rationale for the difference is proposed on the basis of structural studies of the catalyst complexes using ESI-MS.

Original languageEnglish
Pages (from-to)2527-2530
Number of pages4
JournalOrganic letters
Volume7
Issue number13
DOIs
Publication statusPublished - 2005 Dec 1
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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