State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
Org Lett. 2017 Apr 7;19(7):1862-1865. doi: 10.1021/acs.orglett.7b00625. Epub 2017 Mar 28.
A general and practical organocatalytic asymmetric 1,3-dipolar cycloaddition of 3-amino oxindole-based azomethine ylides and α,β-enones has been developed. This reaction delivered spiro[pyrrolidine-2,3'-oxindole] products in high yields with excellent regio- and enantioselectivities (up to 99% yield, >20:1 rr, 99% ee). In addition, an array of spiro[dihydropyrrole-2,3'-oxindoles] were readily accessed by oxidative dehydrogenation. Notably, the inversion of the diastereoselectivity of the spiro[pyrrolidine-oxindole] product could be easily achieved through a facile oxidation-reduction process.
已开发出一种通用且实用的基于 3-氨基氧吲哚的亚胺叶立德和α,β-烯酮的有机催化不对称 1,3-偶极环加成反应。该反应以高产率和优异的区域和对映选择性（高达 99%的收率、>20:1 rr、99%ee）提供了螺[吡咯烷-2,3'-氧吲哚]产物。此外，通过氧化脱氢可以很容易地获得一系列螺[二氢吡咯-2,3'-氧吲哚]。值得注意的是，通过简单的氧化还原过程，可以轻松实现螺[吡咯烷-氧吲哚]产物的非对映选择性反转。
