Zhu Guodong, Wu Shiqi, Bao Xiaoze, Cui Longchen, Zhang Yanpeng, Qu Jingping, Chen Hongbo, Wang Baomin
State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116024, P. R. China.
Chem Commun (Camb). 2017 Apr 25;53(34):4714-4717. doi: 10.1039/c7cc01653k.
An organocatalytic asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides and α,β-ynones has been developed. This reaction afforded spiro[dihydropyrrole-2,3'-oxindole] products in high chemical yields with excellent stereoselectivities (up to 99% yields, >20 : 1 dr and >99% ee). Notably, a series of important spiro[pyrrole-oxindole] derivatives were readily obtained via oxidation of the cycloadducts, thus extending the diversity of the products.
已开发出一种基于3-氨基氧化吲哚的甲亚胺叶立德与α,β-炔酮的有机催化不对称[3+2]环加成反应。该反应以高化学产率和优异的立体选择性（高达99%的产率、>20:1的非对映选择性和>99%的对映体过量）得到螺[二氢吡咯-2,3'-氧化吲哚]产物。值得注意的是，通过环加成产物的氧化很容易得到一系列重要的螺[吡咯-氧化吲哚]衍生物，从而扩展了产物的多样性。
