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Access to 1,2‐Dihydroisoquinolines through Gold‐Catalyzed Formal [4+2] Cycloaddition
Author(s) -
Xin Zhuo,
Kramer Søren,
Overgaard Jacob,
Skrydstrup Troels
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403290
Subject(s) - cycloaddition , aldimine , catalysis , formal synthesis , combinatorial chemistry , disconnection , chemistry , computer science , stereochemistry , organic chemistry , political science , law
A new synthetic route to the privileged 1,2‐dihydroisoquinolines is reported. This method, which relies on a gold‐catalyzed formal [4+2] cycloaddition between ynamides and imines, provides a new retrosynthetic disconnection of the 1,2‐dihydroisoquinoline core by installing the 1,8a CC and 2,3 CN bonds in one step. Both aldimines and ketimines can be used as substrates. In addition, one example of dihydrofuropyridine synthesis is also demonstrated.