1126793-33-6Relevant academic research and scientific papers
Intramolecular carbolithiation reactions for the synthesis of 2,4-disubstituted tetrahydro-quinolines: Evaluation of TMEDA and (-)-sparteine as ligands in the stereoselectivity
Martinez-Estibalez, Unai,Sotomayor, Nuria,Lete, Esther
, p. 1237 - 1240 (2009)
The preparation of 4-substituted 2-phenyltetrahydroquinolines from N-alkenylsubstituted 2-iodoanilines via intramolecular carbolithiation reactions has been investigated. The stereochemical outcome of the carbolithiation reactions depends on the nature of organolithium employed to perform the lithium-halogen exchange, the solvent, or the use of additives, for example, TMEDA or chiral bidentated ligands such as (-)-sparteine. Thus, the 2,4-disubstituted tetrahydroquinolines are obtained with moderate diastereoselectivities (up to 77:23) and with ee up to 94% when Weinreb amide derivatives are used (R) CONMe(OMe)).
