U. Bosche et U. Nubbemeyer, Synthesis of optically active N-allyl amino compounds with defined trisubstituted double bonds, TETRAHEDRON, 55(22), 1999, pp. 6883-6904
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.