The research described in this thesis is aimed at demonstrating the synthetic utility of the
asymmetric amino-Cope rearrangement and highlight its potential for future application
in natural product synthesis.
Using the recently developed asymmetric anionic amino-Cope methodology,
rearrangement of diasteromerically pure 3-amino-l,5-hexadiene substrates provided the
target aldehyde in good yield and with high levels of asymmetric induction (up to 94%
The aldehyde obtained was used for the successful formation of2,4-disubstituted lactones
with no apparent loss of stereochemical integrity. This could lead to a plausible route to
biologically significant compounds....
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.