Controlled synthesis of cis or trans isomers of 1,3-disubstituted tetrahydroisoquinolines and 2,5-disubstituted pyrrolidines.
[reactions: see text] The stereoselective outcome of Pd(II)- or Ag(I)-catalyzed intramolecular N-alkylation to afford 1,3-disubstituted 1,2,3,4-tetrahydroisoquinolines was examined. In the absence of additional substituents, Pd(II) allows a facile access to the cis isomers, while Ag(I) favors formation of the trans isomers. The same observation was made for the synthesis of 2,5-disubstituted pyrrolidines. Possible reasons for the observed stereoselectivities are discussed.
Eustache
Jacques
J
Laboratoire de Chimie Organique et Bioorganique associé au CNRS, Université de Haute-Alsace, Ecole Nationale Supérieure de Chimie de Mulhouse, 3, rue Alfred Werner, F-68093 Mulhouse Cedex, France. jacques.eustache@uha.fr
Van de Weghe
Pierre
P
Le Nouen
Didier
D
Uyehara
Hiroshi
H
Kabuto
Chizuko
C
Yamamoto
Yoshinori
Y