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Paper | Special issue | Vol 88, No. 1, 2014, pp.425-440
Published online, 2nd August, 2013
DOI: 10.3987/COM-13-S(S)46
Synthesis of Tetrahydroquinolines through Intramolecular Carbolithiation Reactions

Oihane García-Calvo, Unai Martínez-Estíbalez, Esther Lete, and Nuria Sotomayor*

*Departamento de Química Orgánica, Facultad de Ciencia y Tecnologia, Universidad del País Vasco, Barrio Sarriena s/n. Leioa (Bizkaia) Bilbao 48940, Spain

Abstract

Cyclization of aryllithiums obtained by iodine-lithium exchange reaction on N-alkenyl 2-iodoanilines allows the synthesis of 4- and 2,4-substituted tetrahydroquinolines. However, the alkene has to be substituted with a stabilizing group for the resulting organolithium to favor the intramolecular carbolithiation. When (–)-sparteine (4) or (+)-sparteine surrogate (5) are used as chiral ligands low levels of enantioselection are obtained. The carbolithiation is completely diastereoselective when an enantiomerically pure precursor is used.