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Catalyzed Tandem Reaction of 3‐Silyloxy‐1,5‐enynes Consisting of Cyclization and Pinacol Rearrangement
Author(s) -
Kirsch Stefan F.,
Binder Jörg T.,
Crone Benedikt,
Duschek Alexander,
Haug Timm T.,
Liébert Clémence,
Menz Helge
Publication year - 2007
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.200604544
Subject(s) - pinacol , tandem , chemistry , sequence (biology) , set (abstract data type) , catalysis , simple (philosophy) , combinatorial chemistry , computer science , organic chemistry , philosophy , materials science , biochemistry , programming language , epistemology , composite material
Au‐spicious! Under silver‐free conditions, simple 3‐silyloxy‐1,5‐enynes were converted into complex cyclopentenes by a gold(I)‐catalyzed sequence that likely proceeds through a carbocyclization followed by a pinacol rearrangement. For the final demetalation step, isopropyl alcohol and N ‐iodosuccinimide are effectively utilized, and the resulting products are set up for a wealth of further reactions.