Asymmetric Hydrogenation of Benzalacetone Catalyzed by RuCl2(TPPTS)2-(S,S)-DPENDS in Water Medium

The asymmetric hydrogenation of benzalacetone catalyzed by ruthenium monophosphine complex RuCl2(TPPTS)2 [TPPTS = P(m-C6H4SO3Na)3] modified by (S,S)-DPENDS (disodium salt of sulfonated (S,S)-1,2-diphenyl-1,2-ethylene-diamine) was investigated in a water medium. Under the optimized conditions, a chemoselectivity of 96.0% for 4-phenyl-3-butene-2-ol and ee value of 71.2% were obtained. The products could be easily obtained by simple extraction with n-hexane, and the catalyst could be reused five times without evident loss of catalytic activity and enantioselectivity.

摘要将水溶性手性二胺䜕(S,S)-1,2-二苯基乙二胺二磺酸钠䜕((S,S)-DPENDS)䜕与钌膦配合物䜕([RuCl2(TPPTS)2]2)䜕原位生成的催化剂用于催化水相中苄叉丙酮的不对称加氢反应.䜕䜕在优化条件下,䜕羰基加氢产物䜕4-苯基-3-丁烯-2-醇的选择性可达䜕96.0%,䜕对映选择性可达䜕71.2%.䜕䜕经正己烷简单萃取后即可实现催化剂与加氢产物的分离,䜕循环使用䜕5䜕次后,䜕目标产物䜕4-苯基-3-丁烯-2-醇选择性和对映选择性没有明显下降.䜕

Graphical abstractThe asymmetric hydrogenation of benzalacetone catalyzed by RuCl2(TPPTS)2-(S,S)-DPENDS in water medium was investigated. The selectivity of 96.0% for 4-phenyl-3-butene-2-ol and ee value of 71.2% were obtained. The catalyst could be reused five times without evident loss of catalytic activity and enantioselectivity.Figure optionsDownload full-size imageDownload as PowerPoint slide