State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University , Tianjin 300071, China.
J Org Chem. 2018 Mar 2;83(5):2714-2724. doi: 10.1021/acs.joc.7b03177. Epub 2018 Feb 12.
A chiral squaramide catalyzed approach constructing spiro-3,4-dihydrocoumarin motif by the enantioselective 1,6-addition/acetalization reactions of 1-oxotetralin-2-carbaldehydes and ortho-hydroxyphenyl-substituted para-quinone methides followed by an oxidation was developed. The reactions proceeded smoothly with a wide range of p-QMs and 1-oxotetralin-2-carbaldehydes to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee).
一种手性方酰胺催化方法，通过 1-氧代四氢萘-2-醛和邻羟基苯基取代的对醌甲醚的对映选择性 1,6-加成/缩醛化反应，构建了螺-3,4-二氢香豆素基序，随后进行氧化。反应在很宽的 p-QMs 和 1-氧代四氢萘-2-醛范围内顺利进行，以高收率和优异的非对映选择性（>19:1 dr）和对映选择性（高达 99%ee）生成相应的产物。
