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Experimental and Theoretical Observations on the Intramolecular Nucleophilic Addition of α‐Amino Carbanions to Arynes: Synthesis of 1‐Aryl‐1,2,3,4‐tetrahydroisoquinolines
Author(s) -
Kaur Manjot,
Sharma Esha,
Singh Amritpal,
Singh Paramjit,
Singh Kamal Nain
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600567
Subject(s) - chemistry , aryne , carbanion , intramolecular force , nucleophile , aryl , lewis acids and bases , nucleophilic addition , medicinal chemistry , amine gas treating , stereochemistry , organic chemistry , computational chemistry , catalysis , alkyl
1‐Aryl‐1,2,3,4‐tetrahydroisoquinolines (THIQ) are key intermediates and products in the pharmaceutical industry. A new method involving intramolecular nucleophilic addition of α‐amino carbanions to in‐situ‐generated arynes in N ‐Boc‐protected (Boc = tert ‐butoxycarbonyl) amine substrates is presented for the synthesis of these compounds. Surprisingly, a similar reaction in Lewis‐acid‐complexed tertiary amines failed. These results have been analysed using quantum chemical calculations on the intermediates involved in the reactions.