A silver-catalyzed spirocyclization of alkynyl silyl enol ethers.
Ring out the old: The cycloisomerization of alkynyl silyl enol ethers proceeds at ambient temperature under the mild conditions of silver catalysis. 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.
Laboratoire de Chimie Organique Synthétique, Institut de Chimie, UMR 7177, Université de Strasbourg, 1 rue Blaise Pascal, BP 296/R8, 67008 Strasbourg-Cedex, France.
Christian
C
Schäfer
Michel
M
Miesch
Laurence
L
Miesch
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry
D000480:Alkynes; D007659:Ketones; D017646:Organosilicon Compounds; D013141:Spiro Compounds; D013388:Succinimides; C008155:N-iodosuccinimide; D012834:Silver