Authors: Goodwin, Nicole Cathleen (2006)The first enantioselective, catalytic vinylogous Mukaiyama-Michael reaction of siloxyfurans with simple a,(3-unsaturated aldehydes has been reported using chiral imidazolidinones. This methodology provides access to enantioenriched y-butenolides, a privileged motif in organic synthesis. The utility of this organocatalytic Mukaiyama-Michael reaction was highlighted by the total syntheses of (-)-spiculisporic acid and (-)-5-epi-spiculisporic acid.
Investigations into the total syntheses of cylindrocyclophanes A and F necessitated
the development of a novel B-alkyl Suzuki cross-coupling of trimethylanilinium salts using
a nickel(O) catalyst and bulky phosphine ligand. This methodology study revealed a very
competitive nickel-catalyzed demethylation pathway, which produced dimethyla...