聚乙二醇400-水介质中水溶性钌膦二胺催化苄叉丙酮的不对称加氢反应

Green and Recyclable Medium for Asymmetric Hydrogenation of Benzalacetone Catalyzed by RuCl_2(TPPTS)_2-(S,S)-DPENDS

在聚乙二醇400-水绿色可循环介质中,以手性二胺(S,S)-1,2-二苯基乙二胺二磺酸钠((S,S)-DPENDS)与非手性钌膦络合物([RuCl2(TPPTS)2]2)原位生成的水溶性钌膦二胺为催化剂,考察了苄叉丙酮的选择性不对称加氢反应.在优化的反应条件下,羰基加氢产物4-苯基-3-丁烯-2-醇的化学选择性和对映选择性分别为98.5%和74.3%.经正己烷萃取后,催化剂即可从产物中分离出来.循环使用5次后,4-苯基-3-丁烯-2-醇化学选择性和对映选择性没有明显下降.

PEG400-H2O was a green and recyclable reaction medium for asymmetric hydrogenation of benzalacetone catalyzed by ruthenium achiral monophosphine complex, RuCl2（TPPTS）2 （TPPTS： P（m-C6H4SO3Na）3）, which was modified by （S,S）-DPENDS （disodium salt of sulfonated （S,S）-1,2-diphenyl-1,2-ethylene-diamine）. Under the optimized conditions, the chemoselectivity for 4-phenyl-3-buten-2-ol was 98.5% with a corresponding ee value of 74.3%. The resulting products could easily be separated from the catalyst by extraction with n-hexane. The catalyst immobilized on PEG400-H2O could be recycled and reused at least five times without significant loss of chemoselectivity and enantioselectivity.