Iodocarbocyclization reaction of β-ketoesters and alkynes

J Barluenga, D Palomas, E Rubio, JM González - Organic Letters, 2007 - ACS Publications
J Barluenga, D Palomas, E Rubio, JM González
Organic Letters, 2007ACS Publications
Iodocyclopentenes are formed at room temperature upon straight reaction of δ-alkynyl-β-
ketoesters with I2 for several hours. Cyclizations involving terminal and substituted (alkyl,
aryl, Br, I) alkynes were accessed. Twelve examples with yields ranging from 20% up to 80%
are reported (out of them eight cases are above 60%). These results present the first
examples of the iodonium-promoted 5-endo-dig carbocyclization of active methyne
substrates onto alkynes.
Iodocyclopentenes are formed at room temperature upon straight reaction of δ-alkynyl-β-ketoesters with I2 for several hours. Cyclizations involving terminal and substituted (alkyl, aryl, Br, I) alkynes were accessed. Twelve examples with yields ranging from 20% up to 80% are reported (out of them eight cases are above 60%). These results present the first examples of the iodonium-promoted 5-endo-dig carbocyclization of active methyne substrates onto alkynes.
ACS Publications
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