Batsomboon Paratchata, Phakhodee Wong, Ruchirawat Somsak, Ploypradith Poonsakdi
Program in Chemical Biology, Chulabhorn Graduate Institute, Vipavadee-Rangsit Highway, Bangkok, Thailand 10210.
J Org Chem. 2009 May 15;74(10):4009-12. doi: 10.1021/jo900504y.
2-Arylchromans were readily prepared from the hetero-Diels-Alder reactions of styrenes with the ortho-quinone methides (o-QMs) which, in turn, were generated by treating the MOM-protected benzylacetate derivatives with p-TsOH immobilized on silica (PTS-Si) in toluene under mild conditions (0 degrees C to rt). The corresponding chromans were obtained in moderate to excellent yields (42-97%) and in moderate to excellent diastereoselectivity (up to >99:1).
通过苯乙烯与邻醌甲基化物（o-QMs）的杂环狄尔斯-阿尔德反应可轻松制备2-芳基苯并二氢吡喃，而邻醌甲基化物又是通过在温和条件（0℃至室温）下，用固定在硅胶上的对甲苯磺酸（PTS-Si）处理甲氧基甲基（MOM）保护的苄基乙酸酯衍生物在甲苯中生成的。相应的苯并二氢吡喃以中等至优异的产率（42-97%）和中等至优异的非对映选择性（高达>99:1）获得。
