One-pot synthesis of pentacyclic diamines from quinolines by a new Zn/AcOH-promoted cascade reaction.
A simple and efficient method for the one-pot synthesis of pentacyclic diamines from quinolines is described. It involves a new Zn/AcOH-promoted cascade reaction, in which two C[bond]C bonds and four to five stereogenic centers are established under mild conditions. The regiochemistry of the dimerization and cyclization step is governed by substituent effects, allowing access to a head-to-head (2, 3) or head-to-tail skeleton (4, 5).
Gauffre
Jean-Christophe
JC
Laboratoire de Chimie des Substances Végétales, LCSV - Institut du Pin, Université Bordeaux I, 351, Cours de la Libération, 33405 Talence-Cedex, France.
Grignon-Dubois
Micheline
M
Rezzonico
Bernadette
B
Léger
Jean-Michel
JM