Synthesis of optically active N-allyl amino compounds with defined trisubstituted double bonds

Optically active acyclic N-allylamino compounds with defined configurated t risubstituted double bonds were generated via a three step sequence. The fi rst crucial step was a two-carbon chain elongation of chiral ol-aminoacid e sters succeeding in a Claisen eater condensation with acetic acid ester eno lates. The so formed beta-ketoesters were subjected to a one pot procedure of an enol trifluoromethanesulfonate generation and a consecutive palladium catalysed cross-coupling: A Stille or a Sonogashira type reaction allowed to generate selectively the trisubstituted E-olefins. (C) 1999 Elsevier Sci ence Ltd. All rights reserved.