Reversal of Diastereoselectivity in Reactions of the Trifluoroacetaldehyde Ethyl Hemiacetal with Enamines and Imines: Metal-Free, Complementary <i>anti</i>- and <i>syn</i>-Selective Synthesis of 4,4,4-Trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones
作者:Kazumasa Funabiki、Kei Matsunaga、Hiroshi Gonda、Hitoshi Yamamoto、Takao Arima、Yasuhiro Kubota、Masaki Matsui
DOI:10.1021/jo101733j
日期:2011.1.7
A complete reversal of diastereoselectivity was observed for reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines, derived from propiophenones, that produce 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones. This process serves as the first reliable, metal-free, complementary anti- and syn-selective method to prepare 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones
对于三氟乙醛乙基半缩醛与衍生自丙苯酮的烯胺和亚胺的反应,观察到了完全非对映选择性的逆转,产生了4,4,4-三氟-1-芳基-3-芳基-2-羟基-2-甲基-1-丁酮。该过程作为第一可靠,无金属的,互补的抗-和顺式,制备4,4,4-三氟-1-芳基-3-羟基-2-甲基-1-丁酮-选择性方法。