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Synthesis 2014; 46(13): 1739-1750
DOI: 10.1055/s-0033-1341239
DOI: 10.1055/s-0033-1341239
paper
Nucleophilic Addition of Lewis Acid Complexed α-Amino Carbanions to Arynes: Synthesis of 1-Aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines
Further Information
Publication History
Received: 13 February 2014
Accepted after revision: 28 March 2014
Publication Date:
12 May 2014 (online)
Abstract
The direct C-1 arylation of N-methyl-1,2,3,4-tetrahydroisoquinolines via coupling of α-amino carbanions derived from Lewis acid complexed tetrahydroisoquinolines and in situ generated arynes is described. This process provides an easy access to the title compounds and a new synthetic route to (±)-cryptostyline alkaloids.
Key words
arylation - arynes - tetrahydroisoquinolines - cryptostyline alkaloids - Lewis acid complexationSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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Many arylation procedures using transition metals, and thus having an obvious drawback are reported.