Related resources
Search for item elsewhere
University researcher(s)
Academic department(s)
OFF-TEMPLATE FUNCTIONALISATION OF CARBOHYDRATES
[Thesis]. Manchester, UK: The University of Manchester; 2012.
Access to files
-
FULL-TEXT.PDF (pdf)
Abstract
The conjugate addition of organometallic reagents to α,β-unsaturated carbonyl compounds has been studied extensively and is now one of the most important methods for carbon-carbon bond formation. In devising a novel approach to the synthesis of C-glycosides such as gilvocarcin M, we had occasion to investigate the conjugate addition reactions of a diverse range of nucleophilic reagents (i.e. cuprate, RMgX, R-Li, NR2 and ylides) with a number of γ-alkoxy-α,β-unsaturated compounds (esters, ketones, aldehydes, nitro and sulfones): a sequence which hitherto has received scant attention. The stereochemical outcome of these conjugate addition reactions has been elucidated and the stereochemical rationale for the observed sense of asymmetric induction is also discussed.