Facile one-pot synthesis of β-enaminoketoesters

ORGN 929

John Nielsen, jn@kvl.dk and Tobias Persson, tp@kvl.dk. Department of Natural Sciences, Bioorganic Chemistry Section, The Royal Veterinary and Agricultural University, Thorvaldsensvej 40, DK-1871 Frederiksberg C, Denmark
One-pot synthesis of β-enaminoketoesters from Weinreb amides has been developed. The reaction proceeds through tandem acyl substitution-conjugate addition by initial attack from the sodium acetylide of ethyl propynoate on a Weinreb amide. The versatility of the reaction was established by array synthesis of β-enaminoketoesters and their use as 1,3-dielectrophiles in cyclocondensation reactions. Regioselective synthesis of heterocyclic structures such as pyrazoles will be presented.