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Furan‐Based o‐ Quinodimethanes by Gold‐Catalyzed Dehydrogenative Heterocyclization of 2‐(1‐Alkynyl)‐2‐alken‐1‐ones: A Modular Entry to 2,3‐Furan‐Fused Carbocycles
Author(s) -
Zhou Liejin,
Zhang Mingrui,
Li Wenbo,
Zhang Junliang
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403709
Subject(s) - furan , chemistry , catalysis , pyridine , modular design , medicinal chemistry , combinatorial chemistry , organic chemistry , computer science , operating system
A strategy for in situ generation of furan‐based ortho ‐quinodimethanes ( o ‐QDMs) by the gold(I)‐mediated dehydrogenative heterocyclization of 2‐(1‐alkynyl)‐2‐alken‐1‐ones in the presence of pyridine N ‐oxide under mild reaction conditions was developed. These in situ furan‐based o ‐QDMs were trapped by electron‐deficient olefins and alkynes, thus furnishing various 2,3‐furan‐fused carbocycles in good yields with high diastereo‐ and regioselectivities.