Single-step synthesis of a radically polymerizable 1,1′-bi-2-naphthol derivative for asymmetric catalysis

Abstract

Abstract:A new polymerizable 1,1 ′ -bi-2-naphthol derivative for polymer-supported catalytic asymmetric synthesis is presented. The synthesis is conducted within a single reaction step, which is a major advantage over other approaches presented in the literature. The ligand-bearing polymer is prepared through copolymerization with N-isopropylacrylamide. Preliminary experiments on the utility in catalytic asymmetric alkylation reactions reveal the accessibility and activity of the polymer-attached catalysts. The stereoselectivity of the reaction is found to be somewhat lower than for reactions performed in the presence of free 1,1 ′ -bi-2-naphthol, and thus requires further optimization. The enantiomeric excess of the reaction products was determined via 1 H NMR spectroscopy after chiral derivatization with (R)--methylbenzyl isocyanate.

Application of Chiral 1,1'-Bi-2-naphthol Polymers in Asymmetric Epoxidation of (E)-α,β-Unsaturated Aryl Ketones

“…首先合成了聚[(S)-3-丙烯酰胺基-2,2'-二羟基-1,1'联 二萘](poly-1) [11] . 随后使用查尔酮作为底物, 用过氧化 氢异丙苯作为氧化剂, 对 α,β-不饱和芳基酮的不对称环 氧化反应进行了反应条件探索.…”