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Gold‐Catalyzed Synthesis of Chroman, Dihydrobenzofuran, Dihydroindole, and Tetrahydroquinoline Derivatives
Author(s) -
Hashmi A. Stephen K.,
Rudolph Matthias,
Bats Jan W.,
Frey Wolfgang,
Rominger Frank,
Oeser Thomas
Publication year - 2008
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.200800210
Subject(s) - heteroatom , moiety , chemistry , catalysis , ether , organic chemistry , combinatorial chemistry , ring (chemistry)
Abstract Different furans containing an ynamide or alkynyl ether moiety in the side chain were prepared. The gold‐catalyzed transformation of these compounds delivered dihydroindole, dihydrobenzofuran, chroman, and tetrahydroquinoline derivatives at room temperature through very fast reactions. Furthermore, the stabilizing effect of the heteroatom directly attached to the intermediate arene oxides led to highly selective reactions, even in the case of only mono‐substituted furans, which is quite different from previous results obtained with non‐heteroatom‐substituted alkynes.