T. Ishihara, K. Yamaguchi, M. Kuroboshi*
Jul 18, 1994
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron Letters
Abstract
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.