Organic letters

Intramolecular Carbolithiation Reactions for the Synthesis of 2, 4-Disubstituted Tetrahydro-quinolines: Evaluation of TMEDA and (−)-Sparteine as Ligands in the …

U Martínez-Estíbalez, N Sotomayor, E Lete

Index: Martinez-Estibalez, Unai; Sotomayor, Nuria; Lete, Esther Organic Letters, 2009 ,  vol. 11,  # 6  p. 1237 - 1240

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Citation Number: 16

Abstract

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, ...