Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia.
J Org Chem. 2013 Aug 16;78(16):8117-22. doi: 10.1021/jo4008223. Epub 2013 Aug 6.
Starting from simple alkylidene oxindoles and nitroketones, a highly stereoselective methodology was developed for the synthesis of spiro-cyclopentaneoxindoles with four consecutive stereogenic centers. Using an organocatalytic cascade of Michael and aldol reactions in the presence of a chiral thiourea catalyst products were obtained in moderate to high yields and excellent enantioselectivities. Nitro, ester, and hydroxyl groups were introduced to the spiro ring, which could be used to facilitate further functionalization of the products.
从简单的亚烷基氧化吲哚和硝基酮出发，开发了一种高立体选择性的方法，用于合成具有四个连续手性中心的螺环戊烷氧化吲哚。在手性硫脲催化剂的存在下，通过迈克尔加成和醛醇缩合的有机催化级联反应，以中等至较高的收率和优异的对映选择性得到产物。可以在螺环上引入硝基、酯基和羟基，以方便进一步对产物进行官能化。
