Catalyzed Tandem Reaction of 3‐Silyloxy‐1,5‐enynes Consisting of Cyclization and Pinacol Rearrangement | Zendy

Kirsch Stefan F. | Zendy; Binder Jörg T. | Zendy; Crone Benedikt | Zendy; Duschek Alexander | Zendy; Haug Timm T. | Zendy; Liébert Clémence | Zendy; Menz Helge | Zendy

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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.

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