TY - JOUR
T1 - 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
AU - Ishihara, Takashi
AU - Yamaguchi, Koichi
AU - Kuroboshi, Manabu
AU - Utimoto, Kiitiro
PY - 1994/7/18
Y1 - 1994/7/18
N2 - 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.
AB - 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.
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U2 - 10.1016/S0040-4039(00)77080-8
DO - 10.1016/S0040-4039(00)77080-8
M3 - Article
AN - SCOPUS:0028237288
SN - 0040-4039
VL - 35
SP - 5263
EP - 5266
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 29
ER -