苯乙酮酸冰片酯的合成及其诱导不对称Henry反应

Synthesis and asymmetric Henry reaction of bornyl phenylglyoxylate

在四乙氧基钛催化下,用天然丰产的冰片为手性源与苯乙酮酸乙酯进行酯交换得到含手性基团的苯乙酮酸冰片酯,苯乙酮酸冰片酯在冰片基的立体控制下与硝基甲烷缩合,主要得到2R-2-羟基-2-苯基-3-硝基丙酸冰片酯,用高效液相色谱法分析了诱导不对称Henry缩合反应效果,其e.e.值为56.5%,用IR1、H NMR1、3C NMR确认了合成物结构。

In the presence of titanium（Ⅳ） ethoxide,the chiral bornal phenylglyoxylate was prepared using transesterification with ethyl phenylglyoxylate and the natural abundant chiral borneol.In the auxiliaries of asymmetric factor,the bornal 2R-2-hydroxy-2-phenyl-3-nitropropionate was synthesized by the Henry reaction with the bornal phenylglyoxylate and nitromethane.The enantioselectivity was analyzed by HPLC,the enantiomeric excess（e.e.） was 56.5%.The structures were confirmed by IR,1H NMR,13C NMR spectroscopy.