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Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines.

ABSTRACT: 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.

SUBMITTER: Chong HS 

PROVIDER: S-EPMC6423956 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines.

Chong Hyun-Soon HS   Chen Yunwei Y  

Organic letters 20131118 23

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. ...[more]

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