A study of the effect of substrate structure on a Claisen-aza-Cope reaction is presented including a rationalisation of the reaction outcome using DFT calculations. An asymmetric version of the reaction is also described that is of relevance to a proposed approach to the communesin family of
![Graphical abstract: Studies on the Claisen rearrangements in the indolo[2,3-b]quinoline system](http://hg.y866.cn/compound/lib/scimg/usr/1/B915677A.jpg)