A novel method for the synthesis of 1-aryltetrahydroisoquinolines

[Display omitted] •A brief and less limited approach relative to the Pictet-Spengler method to 1-aryltetrahydroisoquinolines.•A variety of contrasting routes are available for precursor synthesis.•Chiral, non-racemic products should be available from this method. Carbenium ions generated from substi...

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Bibliographic Details
Published inTetrahedron letters Vol. 58; no. 4; pp. 294 - 297
Main Authors Ghanim, Amany M., Knight, David W., Rutkowski, Piotr M., Osman, Nermine A., Abdel-Fattah, Hanan A., Kadry, Azza M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.01.2017
Elsevier
Subjects
1-Aryltetrahydroisoquinolines
Acid-catalysed
Carbenium ions
Chemistry
Chemistry, Organic
Intramolecular
Physical Sciences
Science & Technology
Trapping
Acid-catalysed
1-Aryltetrahydroisoquinolines
Carbenium ions
Trapping
Intramolecular
TETRAHYDROISOQUINOLINE ANTITUMOR ANTIBIOTICS
ASYMMETRIC-SYNTHESIS
ISOQUINOLINE ALKALOIDS
DERIVATIVES
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Summary:[Display omitted] •A brief and less limited approach relative to the Pictet-Spengler method to 1-aryltetrahydroisoquinolines.•A variety of contrasting routes are available for precursor synthesis.•Chiral, non-racemic products should be available from this method. Carbenium ions generated from substituted benzhydryls using acid catalysis undergo smooth intramolecular trapping by pendant sulfonamide groups to provide excellent yields of 1-aryltetrahydroisoquinolines.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.11.115