Andrew Caerwyn Williams

Synthesis of N-protected amino esters via palladium catalysed allylic substitution

Abstract N-protected allylamines were prepared by palladium catalysed allylic substitution of the corresponding allyl acetates with a range of nitrogen nucleophiles. The so-formed N-protected allylamines were subjected to oxidative cleavage of the alkene to afford N-protected amino acids or esters.

Palladium-catalysed asymmetric allylic substitution: synthesis ofα- and β-amino acids

Methodology has been established for the formation of enantiomerically enriched α-amino acids using palladium-catalysed allylic amination. The formation of enantiomerically enriched allylamines has been achieved with high enantioselectivity. Oxidative cleavage of the allylamines provides arylglycine and glutamic acid derivatives. Additionally, enantiomerically enriched β-amino acids have been prepared in high enantiomeric excess. Palladium-catalysed asymmetric allylic substitution is used as the key synthetic transformation.