New methodology involving allylic substitution and conjugate addition reactions

Chapter one reviews routes to the generation of α-aminophosphonates and α-aminophosphonic acids. These biologically important compounds are synthesised in both racemic and enantiomerically enriched forms. The second chapter describes the results of conjugate addition reactions of lower order cuprates to diethylvinylphosphonate followed by an electrophilic quench to give a range of alkylphosphonates. The third and fourth chapters are concerned with the generation of enantiomencally enriched α-aminophosphonates and α-aminoesters via palladium catalysed allylic substitution reactions With allyl acetate the resulting products were isolated with an enantiomeric excess of up to 19%. With 1,3-diphenyl-2-propenyl acetate products with both high diastereomeric and enantiomeric excesses were isolated with the best being 75 % de and 97 % ee.