T. Yamashita, Eizo Kagigaki, Nozomu Takahashi
Apr 1, 1983
Citations
0
Influential Citations
4
Citations
Journal
Macromolecular Chemistry and Physics
Abstract
Poly[(3S)-1,2,3,4-tetrahydroisoquinoline-2,3-diylmethylene] (4) and (3S)-3-(1,2,3,4-tetrahydroisoquinolin-2-ylmethyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline (7) were prepared using (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (1) as starting material. The optically active amines 4 and 7 were used as asymmetric catalysts for the addition of thiophenol (8a), 4-tert-butylthiophenol (8b), or 4-chlorothiophenol (8c) to 2-cyclohexen-1-one (9). 4 yielded 3-phenylthiocyclohexanone (10a) with the highest optical yield of 24% at −25°C, showing a marked polymer effect with respect to enantiomeric excess.