Controlled Synthesis of Cis or Trans Isomers of 1,3-Disubstituted Tetrahydroisoquinolines and 2,5-Disubstituted Pyrrolidines

摘要

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 substit-uents, 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.