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Gold(I)‐Catalysed Azepine Synthesis from Propargyl Acetals and Aryl Azides
Author(s) -
Evjen Sigvart,
Fiksdahl Anne
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.201600319
Subject(s) - azepine , chemistry , propargyl , imine , aryl , cycloaddition , acetal , azide , combinatorial chemistry , organic chemistry , catalysis , alkyl
Gold(I)‐catalysed reactions of phenylpropargyl acetals and aryl azides gave trans ‐3,6‐methoxy‐1,4,5‐triaryl‐4,5‐dihydro‐azepine products (78–94 %) in a highly diastereoselective manner. Two units of propargyl acetal and one unit of aryl azide are incorporated into the azepine product. The reaction proceeds by a sequential two‐step pathway via an activated Z ‐2‐methoxy vinyl imine intermediate, with a final [4+3] cycloaddition. The imine intermediate could be isolated and used for the further selective preparation of unsymmetrically substituted azepines. The results described here contribute to an improved understanding of the gold(I)‐catalysed reactions of highly reactive propargyl acetals, which undergo a diversity of selective cyclisation reactions with different reactants.