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 Citations (Scopus)

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

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Isoquinolines
Regioselectivity
Cyclization
isoquinoline

Keywords

  • Condensation
  • Cyclization
  • Halotetrahydroisoquinoline
  • Pictet-Spengler

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Regioselectivity of Pictet-Spengler cyclization : Synthesis of halotetrahydroisoquinolines. / Cho, Su Dong; Song, Sang Yong; Hur, Eun Joo; Chen, Ma; Joo, Woo Hong; Falck, J R; Yoon, Yong Jin; Shin, Dong Soo.

In: Tetrahedron Letters, Vol. 42, No. 36, 03.09.2001, p. 6251-6253.

Research output: Contribution to journalArticle

Cho, SD, Song, SY, Hur, EJ, Chen, M, Joo, WH, Falck, JR, Yoon, YJ & Shin, DS 2001, 'Regioselectivity of Pictet-Spengler cyclization: Synthesis of halotetrahydroisoquinolines', Tetrahedron Letters, vol. 42, no. 36, pp. 6251-6253. https://doi.org/10.1016/S0040-4039(01)01189-3
Cho, Su Dong ; Song, Sang Yong ; Hur, Eun Joo ; Chen, Ma ; Joo, Woo Hong ; Falck, J R ; Yoon, Yong Jin ; Shin, Dong Soo. / Regioselectivity of Pictet-Spengler cyclization : Synthesis of halotetrahydroisoquinolines. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 36. pp. 6251-6253.
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AU - Chen, Ma

AU - Joo, Woo Hong

AU - Falck, J R

AU - Yoon, Yong Jin

AU - Shin, Dong Soo

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