Chapter One reviews the use of scandium and lanthanide
trifluoromethanesulfonates (triflates) in organic synthesis. Their ability to act
as Lewis acids and so promote a wide variety of reactions are illustrated. In
particular the review highlights the advantages of scandium and lanthanide
triflates over more conventional Lewis acids, such as aluminium(I1I)
Chapter Two describes the use of scandium and lanthanide trifiates in
the reaction of acetals with amines to produce imines. The extension of this
methodology to the synthesis of nitrogen-containing heterocycles such as
isoindolones, isoquinolinones and ~-carboline derivatives are elaborated on.
Some limitations of the methodology and the problems encountered with its
application to the synthesis of enamines are covered.
Chapter Three reports our approach to a novel synthesis of ~-carboline
derivatives. The formylation of indole-3-acetic acid derivatives in the 2-
position proved difficult and several approaches to this problem are
discussed. The attempted cyclisation of imines prepared from 2-formyl- and 2-
acetyl-3-indolyl acetic acid compounds are also covered. Chapter Four describes a modified Clauson-Kaas pyrrole procedure
using trimethylsilyl trifiate. The selection of reaction conditions in an effort to
optimise the procedure are discussed.
Chapter Five provides full experimental procedures and analytical data
for the reactions described in Chapters Two, Three and Four.
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.