Misc.

Jul 18, 1994

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

Tetrahedron Letters
  • Takashi Ishihara
    • ,
  • Koichi Yamaguchi
    • ,
  • Manabu Kuroboshi
    • ,
  • Kiitiro Utimoto
Volume
35
Number
29
First page
5263
Last page
5266
Language
English
Publishing type
DOI
10.1016/S0040-4039(00)77080-8
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. © 1994.
Link information
DOI
https://doi.org/10.1016/S0040-4039(00)77080-8
ID information
  • DOI : 10.1016/S0040-4039(00)77080-8
  • ISSN : 0040-4039
  • SCOPUS ID : 0028237288
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