A stereoselective route to polysubstituted tetrahydroquinolines by benzotriazole-promoted condensation of aliphatic aldehydes and aromatic amines
By the promotion of benzotriazole (20 mol %), two molecules of anilines (or other arylamines) and two molecules of phenylacetaldehyde (or o-bromophenylacetaldehyde) condensed to give a series of 1,2,3,4-tetrahydroquinolines in a stereoselective manner. By the catalysis of SmI(2) or SmI(3), the N-(alpha-aminoalkyl)benzotriazoles derived from anilines and (R)-glyceraldehyde acetonide dissociated to the corresponding iminium and enamine species, which underwent asymmetric [4 + 2] cycloadditions to give optically active tetrahydroquinolines.
Talukdar
S
Department of Chemistry, National Taiwan University, Taipei, Taiwan 106, Republic of China.
Chen
CT
Fang
JM