This thesis describes work carried out towards the synthesis of novel C₂
symmetric guanidine bases and their application to the catalysis of the nitroaldol and nitro-Michael reactions.
The following achievements were made.
I) The synthesis of a family of novel C₂ symmetric guanidine bases prepared from the addition of guanidine to (6S)-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-1-en-3-one. The a,β-unsaturated ketone is prepared from (S)-(-)-malic acid.
2) Investigations were performed into the catalysis of the nitroaldol reaction of
nitromethane to isopentanal and the nitro-Michael reaction of 2-nitropropane to
trans-chalcone during which moderate enantioselectivity was observed.
3) Work was carried out on the development of a new family of guanidine bases
intended to be more efficient asymmetric catalysts.