苯基碳酸烯丙酯类化合物的合成及其在手性仲胺拆分中的应用

Synthesis of Phenylallyl Carbonate and Its Application in Chiral Secondary Amine Resolution

以酚类化合物和氯化烯丙基甲酯为原料,合成了三种苯基碳酸烯丙酯化合物[1a～1c,其中2-甲氧基苯基碳酸烯丙酯(1b)为新化合物]。以1a～1c为酰基供体,在甲苯中经Novozyme 435酶催化对消旋的1-甲基-6,7-二甲氧基四氢异喹啉(2)进行拆分,得到手性仲胺S-2和R-2,转化率近50%,R-2的对映选择性>99%,其结构经1H NMR和13C NMR表征。

Three phenylallyl carbonate compounds[ 1a -1c, 2-methoxy-phenylallyl carbonate（lb） was new compound] were synthesized by the reaction of phenol compounds and allyl methyl chloride. The structures were characterized by 1H NMR and 13C NMR. S-2 and R-2（e. e. 〉99% ） in about 50% conversion were obtained by enzymatic kinetic resolution of 1-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline（2） using 1a-1c as the acylating reagent and Novozyme 435 as the lipase catalyst.