Indolisation of 1-decalone and the reactions of the products with oxygen and with nucleophiles

Abstract

The regioselectivity of the Fischer indolisation of trans-1-decalone has been examined in order to define conditions which select either indole or indolenine products. During the reactions aerial oxidation may occur and this can lead to some unexpected rearrangements. In addition, the reactions of the indolenines with nucleophiles have been studied with particular reference to the stereoselectivity of the additions.