Institut für Organische Chemie , Universität Leipzig , Johannisallee 29 , 04103 Leipzig , Germany.
Org Lett. 2018 May 18;20(10):3119-3123. doi: 10.1021/acs.orglett.8b01205. Epub 2018 May 9.
The first Sc(OTf)-catalyzed dehydration of 2-hydroxy oxime ethers to generate benzylic stabilized 1-azaallyl cations, which are captured by 1,3-carbonyls, is described. A subsequent addition of primary amines in a sequential three-component reaction affords highly substituted and densely functionalized tetrahydroindeno[2,1- b]pyrroles as single diastereomers with up to quantitative yield. Thus, three new σ-bonds and two vicinal quaternary stereogenic centers are generated in a one-pot operation.
本文首次报道了 Sc(OTf) 催化的 2-羟基肟醚的脱水反应，生成苄基稳定的 1-氮杂丙烯阳离子，后者被 1,3-二羰基化合物捕获。在随后的三组分反应中，伯胺的加成以高产率得到高度取代和稠合官能化的四氢茚并[2,1- b]吡咯，作为单一非对映异构体。因此，一锅法中生成了三个新的 σ 键和两个相邻的季立体中心。
