Chemical and Pharmaceutical Bulletin p. 430 - 433 (1998)
Update date:2022-08-04
Topics:
Shinohara, Tatsumi
Takeda, Akira
Toda, Jun
Sano, Takehiro
The conformation of the piperideine ring in 1-benzyl-1,2,3,4- tetrahydroisoquinolines was determined as 2H3 form with a pseudoaxial position of the 1-benzyl group by circular dichroism (CD) spectral comparison with 1-methyl-1,2,3,4-tetrahydroisoquinolines. The chiral center at C-1 of 1,2,3,4-tetrahydroisoquinoline (TIQ) was constructed in an unambiguous manner by applying a new method of TIQ synthesis utilizing the Pummerer reaction as a key step. Enantiomerically pure (R)- and (S)-1-methyl- and 1- benzyltetrahydroisoquinolines (1) were prepared starting from readily available chiral amines (2) in good overall yields.
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