Asymmetric reduction of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones with lithium aluminum hydride or diisobutylaluminum hydride. Highly stereoselective synthesis of 2-fluoro-2-(trifluoromethyl)-1,3-diols

Takashi Ishihara, Koichi Yamaguchi, Manabu Kuroboshi, Kiitiro Utimoto

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The syn and anti isomers of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones are reduced in a highly 1,2-syn diastereoselective manner with lithium aluminum hydride or diisobutylaluminum hydride in tetrahydrofuran at -78 °C, affording 1,2-syn-2,3-syn- and 1,2-syn-2,3-anti-2-fluoro-2-(trifluoromethyl)-1,3-diols, respectively, in excellent yields. High 1,2-syn stereoselectivity in the reduction can be ascribed to the presence of the 2-trifluoromethyl substituent.

Original languageEnglish
Pages (from-to)5263-5266
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number29
DOIs
Publication statusPublished - Jul 18 1994
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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