Regioselectivity of Pictet-Spengler cyclization: Synthesis of halotetrahydroisoquinolines

Su Dong Cho, Sang Yong Song, Eun Joo Hur, Ma Chen, Woo Hong Joo, J R Falck, Yong Jin Yoon, Dong Soo Shin

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

The regioselectivity of the Pictet-Spengler cyclization for the synthesis of isoquinolines depends on the aryl substituent at C-2. The ratio of halotetrahydroisoquinoline 4 to isoquinoline 3 increases with increasing electrophilicity of the aromatic ring (H≪I<Br<Cl).

Original languageEnglish (US)
Pages (from-to)6251-6253
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number36
DOIs
StatePublished - Sep 3 2001

    Fingerprint

Keywords

  • Condensation
  • Cyclization
  • Halotetrahydroisoquinoline
  • Pictet-Spengler

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Cho, S. D., Song, S. Y., Hur, E. J., Chen, M., Joo, W. H., Falck, J. R., Yoon, Y. J., & Shin, D. S. (2001). Regioselectivity of Pictet-Spengler cyclization: Synthesis of halotetrahydroisoquinolines. Tetrahedron Letters, 42(36), 6251-6253. https://doi.org/10.1016/S0040-4039(01)01189-3