Stereoselective and Regioselective Intramolecular Friedel–Crafts Reaction of Aziridinium Ions for Synthesis of 4‑Substituted Tetrahydroisoquinolines

Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel–Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziridinium ions as the key intermediates in the L...

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Bibliographic Details
Published in:Organic letters 2013-12, Vol.15 (23), p.5912-5915
Main Authors: Chong, Hyun-Soon, Chen, Yunwei
Format: Article
Language:English
Subjects:
Aziridines - chemistry
Catalysis
Lewis Acids - chemistry
Molecular Structure
Stereoisomerism
Tetrahydroisoquinolines - chemical synthesis
Tetrahydroisoquinolines - chemistry
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Summary:Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel–Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziridinium ions as the key intermediates in the Lewis acid catalyzed FC reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4013537