RESUMO
Highly stereoselective syntheses of chiral indolines and tetrahydroquinolines are achieved by combining the asymmetric Zn-mediated allylation of chiral N-tert-butanesulfinyl imines with efficient intramolecular C-N cross-coupling. Herein, the advantages of such a synthetic strategy are illustrated by the synthesis of indolines and tetrahydroquinolines with quaternary stereocenters and multi-substituted 1-oxo-1,2,3,4-tetrahydroisoquinolines.
RESUMO
Highly diastereoselective palladium catalyzed cinnamylation of N-tert-butanesulfinyl imines with cinnamyl acetates has been established to provide enantioenriched ß-aryl homoallylic amines. The synthetic application of this stragety has been successfully demonstrated in the concise total syntheses of antitumor natural products (+)-lycoricidine and (+)-7-deoxypancratistatin.
RESUMO
A highly efficient method for the asymmetric synthesis of chiral quaternary carbon-containing homoallylic and homopropargylic amines under mild conditions was achieved with good yields and high diastereoselectivities.