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Gold(I)‐Catalyzed Cycloisomerization of 3‐Methoxy‐1,6‐enynes Featuring Tandem Cyclization and [3,3]‐Sigmatropic Rearrangement
Author(s) -
Bae Hyo J.,
Baskar Baburaj,
An Sang E.,
Cheong Jae Y.,
Thangadurai Daniel T.,
Hwang InChul,
Rhee Young H.
Publication year - 2008
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.200705117
Subject(s) - cycloisomerization , tandem , sigmatropic reaction , catalysis , reactivity (psychology) , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , materials science , medicine , alternative medicine , pathology , composite material
Golden reactivity : A new gold(I)‐catalyzed cycloisomerization of 3‐methoxy‐1,6‐enynes was discovered. Structurally simple 3‐methoxy‐1,6‐enynes engage in a tandem cyclization/[3,3]‐sigmatropic rearrangement to deliver a variety of 1‐methoxy‐1,4‐cycloheptadienes (see scheme). Notably, the reaction can be performed under very mild conditions and the synthetic utility of this reaction was demonstrated by facile conversion of the product into various cyclohept‐4‐en‐1‐ones.