posted on 2013-08-06, 14:05authored byRyan J. Davoile
This thesis describes the use of bimetallic alkyne complexes for use in variants of the
Nicholas reaction. The heterobimetallic core provides a source of chiral control unlike
previous protocols reported in the literature, as stereocontrol arises from the inherently
chiral cobalt-molybdenum core of these complexes and not from an external source.
The inherently chiral heterobimetallic complexes were utilised as efficient chiral
auxiliaries for nucleophilic additions to both propargylic alkene and Nicholas salt
complexes with a degree of stereocontrol also extending to intramolecular addition.
1,3-Dipolar cycioaddition to homo bimetallic and heterobimetallic enyne complexes to
obtain isoxazoline ring systems was investigated, following a report in the literature.
A novel homobimetallic 1,3-dipole was synthesised on opening of a cyclopropane,
subsequel1tly trapping with a series of aldehyde and imines to efficiently form
tetrahydrofuran and pyrrolidine ring structures.
Chapter 1: An overview of developments of homobimetallic alkyne complexes in the
Nicholas reaction as reported in the literature.
Chapter 2: Highlights our research into the use of bimetallic alkyne complexes for use in
organic synthesis.
Chapter 3: Provides experimental data for our studies.