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Rh‐Catalyzed [5+1] and [4+1] Cycloaddition Reactions of 1,4‐Enyne Esters with CO: A Shortcut to Functionalized Resorcinols and Cyclopentenones
Author(s) -
Fukuyama Takahide,
Ohta Yuko,
Brancour Célia,
Miyagawa Kazusa,
Ryu Ilhyong,
Dhimane AnneLise,
Fensterbank Louis,
Malacria Max
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.201200045
Subject(s) - enyne , cycloaddition , moiety , chemistry , alkyne , catalysis , resorcinol , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry
We have developed novel Rh‐catalyzed [ n +1]‐type cycloadditions of 1,4‐enyne esters, which involve an acyloxy migration as a key step. The efficient preparation of functionalized resorcinols, including biaryl derivatives, from readily available 1,4‐enyne esters and CO was achieved by Rh‐catalyzed [5+1] cycloaddition accompanied by 1,2‐acyloxy migration. When enyne esters had an internal alkyne moiety, the reaction proceeded by a [4+1]‐type cycloaddition involving 1,3‐acyloxy migration, leading to cyclopentenones.