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A Silver‐Catalyzed Spirocyclization of Alkynyl Silyl Enol Ethers
Author(s) -
Schäfer Christian,
Miesch Michel,
Miesch Laurence
Publication year - 2012
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.201200116
Subject(s) - cycloisomerization , enol , silylation , catalysis , chemistry , iodide , ring (chemistry) , silver iodide , methyl iodide , medicinal chemistry , organic chemistry , bicyclic molecule , iodine , layer (electronics) , silver halide
Ring out the old : The cycloisomerization of alkynyl silyl enol ethers proceeds at ambient temperature under the mild conditions of silver catalysis (see scheme). Mono‐ or bicyclic spiro compounds can be obtained by 5‐ exo ‐dig reactions. Trapping the vinyl silver species with an iodide source, such as N ‐iodosuccinimide (NIS), afforded the alkenyl iodide derivatives.